[ CAS No. 693-05-0 ] {[proInfo.proName]}

Name: 693-05-0|3-(Methylamino)propanenitrile|97%
Brand: Ambeed
SKU: A370808
Rating: 95 (35 reviews)

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 693-05-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 693-05-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 693-05-0 ]

SDS Specification

Alternatived Products of [ 693-05-0 ]

Product Details of [ 693-05-0 ]

CAS No. :	693-05-0	MDL No. :	MFCD00001954
Formula :	C₄H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UNIJBMUBHBAUET-UHFFFAOYSA-N
M.W :	84.12	Pubchem ID :	69656
Synonyms :

Calculated chemistry of [ 693-05-0 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	23.89
TPSA :	35.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.19
Log Po/w (XLOGP3) :	-0.51
Log Po/w (WLOGP) :	0.12
Log Po/w (MLOGP) :	-0.33
Log Po/w (SILICOS-IT) :	-0.06
Consensus Log Po/w :	0.08

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.09
Solubility :	104.0 mg/ml ; 1.24 mol/l
Class :	Highly soluble
Log S (Ali) :	0.23
Solubility :	141.0 mg/ml ; 1.68 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-1.1
Solubility :	6.62 mg/ml ; 0.0787 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.23

Safety of [ 693-05-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P271-P264-P280-P312-P337+P313-P305+P351+P338-P362+P364-P332+P313-P302+P352+P312-P304+P340+P312-P501	UN#:	N/A
Hazard Statements:	H312+H332-H303-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 693-05-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 693-05-0 ]
Downstream synthetic route of [ 693-05-0 ]

[ 693-05-0 ] Synthesis Path-Upstream 1~5

1
[ 107-13-1 ]
[ 74-89-5 ]
[ 693-05-0 ]

Yield	Reaction Conditions	Operation in experiment
83.5%	at 15℃;	below 15 ,160.8 g (3.0 mol, 99percent) of acrylonitrile was dropped into 345.1 g (3.0 mol, 27percent) ofMethylamine solution was stirred, then ethanol was distilled off under atmospheric pressure,Then vacuum distillation to give a fraction of 210.6g,This fraction is 3-methylaminopropionitrile, yield 83.5percent;
80%	at 15℃;	1 15 °C or less, 200 g (3.77 mol, 99percent) of acrylonitrile was dropped into 433.7 g (3.77 mol, 27percent) of a solution of methylamine, stirred, and then distilled to ethanol, and then distilled under reduced pressure gave 3-methylaminopropionitrile 253g, yield 80percent;

Reference： [1] Kinetics and Catalysis, 2010, vol. 51, # 5, p. 653 - 656
[2] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 1, p. 87 - 91
[3] Patent: CN106632280, 2017, A, . Location in patent: Paragraph 0023; 0024; 0025
[4] Patent: CN108003141, 2018, A, . Location in patent: Paragraph 0032; 0035
[5] Liebigs Annalen der Chemie, 1980, # 9, p. 1438 - 1447
[6] Journal of the Chemical Society, 1945, p. 399,401
[7] Journal of the American Chemical Society, 1946, vol. 68, p. 1218
[8] Journal of the American Chemical Society, 1949, vol. 71, p. 3337,3339, 3340
[9] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1978, p. 1130 - 1134
[10] Journal of the American Chemical Society, 1971, vol. 93, p. 5542 - 5551
[11] Journal of Heterocyclic Chemistry, 1964, vol. 1, p. 260 - 262
[12] , 1971, vol. 7, p. 2210 - 2213[13] Zhurnal Organicheskoi Khimii, 1971, vol. 7, p. 2129 - 2132
[14] Catalysis Communications, 2011, vol. 12, # 9, p. 808 - 812
[15] Patent: US8367870, 2013, B2, . Location in patent: Paragraph 0208; 0209; 0210; 0211
[16] Patent: US9133306, 2015, B2, . Location in patent: Page/Page column 21

2
[ 19836-78-3 ]
[ 693-05-0 ]

Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 34, p. 4857 - 4858

3
[ 67-56-1 ]
[ 107-13-1 ]
[ 74-89-5 ]
[ 693-05-0 ]

Reference： [1] Journal of the Chemical Society, 1945, p. 399,401
[2] Patent: US2451852, 1945, ,
[3] Angewandte Chemie, 1949, vol. 61, p. 234 Anm.131
[4] Patent: US1992615, 1932, ,
[5] Patent: FR742358, , ,
[6] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 20, p. 346

4
[ 693-05-0 ]
[ 64-17-5 ]
[ 2213-08-3 ]

Reference： [1] Liebigs Annalen der Chemie, 1980, # 9, p. 1438 - 1447
[2] Journal of the Chemical Society, 1945, p. 399,401

5
[ 693-05-0 ]
[ 89-61-2 ]
[ 15950-17-1 ]
[ 81676-71-3 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 295 - 303[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 2, p. 342 - 352

[ 693-05-0 ] Synthesis Path-Downstream 1~88

1
[ 628-20-6 ]
[ 693-05-0 ]
[ 1859-29-6 ]

Reference： [1]Patent: US2775589,1955,

2
[ 693-05-0 ]
[ 64-17-5 ]
[ 2213-08-3 ]

Reference： [1]Liebigs Annalen der Chemie,1980,p. 1438 - 1447
[2]Journal of the Chemical Society,1945,p. 399,401

3
[ 693-05-0 ]
[ 5029-21-0 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5428

4
[ 693-05-0 ]
[ 6291-84-5 ]

Yield	Reaction Conditions	Operation in experiment
79.1%	With lithium aluminium tetrahydride; In diethyl ether;Reflux;	210.3g (2.50mol) 3-methylaminopropionitrile dripped into solution94.9 g (2.50 mol) of lithium aluminum hydride4L ether solution,Heated to reflux,Then slowly dropping 25% sodium hydroxide solution and distilled water,Insoluble matter was filtered off and the ether was recovered by atmospheric distillation.174.3 g of N-methyl-1,3-propanediamine was distilled off under reduced pressure to give a yield of 79.1%

Reference： [1]Patent: CN106632280,2017,A .Location in patent: Paragraph 0023; 0024; 0026; 0030; 0031; 0032
[2]Journal of the American Chemical Society,1956,vol. 78,p. 1945
[3]Journal of the American Chemical Society,1946,vol. 68,p. 1218

5
[ 693-05-0 ]
[ 108-94-1 ]
[ 16283-58-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 151 - 159

6
[ 693-05-0 ]
[ 76-83-5 ]
[ 22100-69-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1968,vol. 4,p. 2048 - 2049
Zhurnal Organicheskoi Khimii,1968,vol. 4,p. 2120 - 2122

7
[ 693-05-0 ]
[ 1147550-11-5 ]
[ 98-88-4 ]
[ 30381-19-2 ]

Reference： [1]Zeitschrift fur Chemie,1970,vol. 10,p. 390 - 391

8
[ 693-05-0 ]
[ 103-72-0 ]
[ 30380-98-4 ]

Reference： [1]Zeitschrift fur Chemie,1970,vol. 10,p. 390 - 391

9
[ 693-05-0 ]
[ 611-19-8 ]
[ 20749-62-6 ]

Reference： [1]Bulletin de la Societe Chimique de France,1968,p. 310 - 313

10
[ 693-05-0 ]
[ 78-94-4 ]
[ 18864-43-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1974,vol. 10,p. 710 - 715
Zhurnal Organicheskoi Khimii,1974,vol. 10,p. 706 - 712

11
[ 693-05-0 ]
[ 105-36-2 ]
[ 24286-82-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3117 - 3126
[2]Journal of medicinal and pharmaceutical chemistry,1961,vol. 4,p. 1 - 19

12
[ 693-05-0 ]
[ 530-93-8 ]
[ 18121-20-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 151 - 159

13
[ 693-05-0 ]
[ 7073-36-1 ]
[ 22977-90-8 ]

Reference： [1]Patent: FR1520925,1968,
Chem.Abstr.,1969,vol. 71

14
[ 693-05-0 ]
[ 624-83-9 ]
[ 20055-22-5 ]

Reference： [1]Journal of the Chemical Society C: Organic,1968,p. 2050 - 2055

15
[ 693-05-0 ]
[ 556-61-6 ]
[ 4983-32-8 ]

Reference： [1]Zeitschrift fur Chemie,1970,vol. 10,p. 390 - 391

16
[ 693-05-0 ]
[ 3659-66-3 ]
[ 31896-22-7 ]

Reference： [1]Patent: DE1946112,1971,
Chem.Abstr.,1971,vol. 74

17
[ 75-15-0 ]
[ 693-05-0 ]
[ 97-00-7 ]
[ 25675-94-9 ]

Reference： [1]Patent: FR1583038,1969,

18
[ 693-05-0 ]
[ 39893-50-0 ]
[ 23742-98-5 ]

Reference： [1]Patent: DE1802739,1969,
Chem.Abstr.,1969,vol. 71

19
[ 693-05-0 ]
[ 57-06-7 ]
[ 30380-97-3 ]

Reference： [1]Zeitschrift fur Chemie,1970,vol. 10,p. 390 - 391

20
[ 693-05-0 ]
[ 535-11-5 ]
[ 67744-35-8 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1961,vol. 4,p. 1 - 19
[2]Polish Journal of Chemistry,1978,vol. 52,p. 1023 - 1028

21
[ 693-05-0 ]
[ 4016-85-7 ]
N-(2-Benzoyl-4-chloro-phenyl)-2-[(2-cyano-ethyl)-methyl-amino]-acetamide [ No CAS ]

Reference： [1]Patent: US3950383,1976,A

22
[ 693-05-0 ]
[ 6021-21-2 ]
[ 59049-40-0 ]

Reference： [1]Patent: US3950383,1976,A
[2]Patent: US3928415,1975,

23
[ 693-05-0 ]
[ 502-42-1 ]
[ 16313-46-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 151 - 159

24
[ 15045-02-0 ]
[ 693-05-0 ]
[ 108440-20-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 976 - 980
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 1207 - 1211

25
[ 4587-00-2 ]
[ 693-05-0 ]
[ 78563-49-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 976 - 980
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 1207 - 1211

26
[ 4524-93-0 ]
[ 693-05-0 ]
[ 72104-46-2 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 19 - 25

27
[ 693-05-0 ]
[ 13623-94-4 ]
3-[((E)-1-Amino-2-nitro-vinyl)-methyl-amino]-propionitrile [ No CAS ]

Reference： [1]Archiv der Pharmazie,1986,vol. 319,p. 161 - 167

28
[ 97-07-4 ]
[ 693-05-0 ]
[ 30388-44-4 ]
[ 81689-46-5 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

29
[ 97-07-4 ]
[ 693-05-0 ]
[ 81689-46-5 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

30
[ 693-05-0 ]
[ 16588-02-6 ]
[ 85020-87-7 ]
[ 81676-74-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

31
[ 693-05-0 ]
[ 16588-02-6 ]
[ 81676-74-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

32
[ 693-05-0 ]
[ 82-34-8 ]
[ 82-38-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1986,p. 939 - 942
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 1046 - 1049
[2]Journal of Organic Chemistry USSR (English Translation),1986,p. 939 - 942
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 1046 - 1049

33
[ 693-05-0 ]
[ 82-44-0 ]
[ 82-38-2 ]

34
[ 693-05-0 ]
[ 137-47-3 ]
[ 68528-28-9 ]
[ 81676-73-5 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

35
[ 693-05-0 ]
[ 137-47-3 ]
[ 81676-73-5 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

36
[ 693-05-0 ]
[ 5464-11-9 ]
[ 99646-01-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1985,p. 1255 - 1264

37
[ 693-05-0 ]
[ 121918-49-8 ]
3-[(5-Acetyl-2-methyl-3-oxo-6-phenyl-2,3-dihydro-pyridazin-4-yl)-methyl-amino]-propionitrile [ No CAS ]

Reference： [1]Synthesis,1994,p. 669 - 671

38
[ 693-05-0 ]
[ 66109-94-2 ]
[ 87422-44-4 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1983,vol. 19,p. 719 - 723
Khimiya Geterotsiklicheskikh Soedinenii,1983,vol. 19,p. 899 - 903

39
[ 693-05-0 ]
[ 66109-95-3 ]
[ 87422-45-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1983,vol. 19,p. 719 - 723
Khimiya Geterotsiklicheskikh Soedinenii,1983,vol. 19,p. 899 - 903

40
[ 693-05-0 ]
[ 167391-50-6 ]
[ 72104-44-0 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 19 - 25

41
[ 693-05-0 ]
[ 39061-32-0 ]
[ 89393-98-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1983,p. 2273 - 2281
Zhurnal Organicheskoi Khimii,1983,vol. 19,p. 2591 - 2600
[2]Journal of Organic Chemistry USSR (English Translation),1983,p. 2273 - 2281
Zhurnal Organicheskoi Khimii,1983,vol. 19,p. 2591 - 2600

42
[ 693-05-0 ]
[ 3663-81-8 ]
[ 79959-06-1 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 19 - 25

43
[ 693-05-0 ]
[ 52559-36-1 ]
[ 89393-98-6 ]

44
[ 693-05-0 ]
[ 4116-90-9 ]
[ 2382-08-3 ]
[ 54229-22-0 ]

45
[ 693-05-0 ]
[ 51867-03-9 ]
4-(N-methyl-N-2'-cyanoethyl)amino-1-benzoyl-2,2a,3,4-tetrahydrobenz<cd>indol-5(1H)-one [ No CAS ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 9517 - 9524

46
[ 693-05-0 ]
[ 104-12-1 ]
[ 91090-02-7 ]

Reference： [1]Journal of Agricultural and Food Chemistry,1994,vol. 42,p. 413 - 422

47
[ 693-05-0 ]
[ 4023-34-1 ]
[ 98902-16-0 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 19 - 25

48
[ 693-05-0 ]
[ 98-88-4 ]
[ 23873-66-7 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 19 - 25

49
[ 693-05-0 ]
[ 126-81-8 ]
[ 90043-98-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 287 - 290

50
[ 693-05-0 ]
[ 5135-30-8 ]
[ 72648-38-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	at 20℃; for 120h;	A solution of 3j46 (1.0 g, 2.37 mmol) in 10 mL of 3-(methylamino)propionitrile was stirred at room temperature for 5 days. The reaction mixture was poured into diethyl ether (50 mL). The ether layer was decanted and the resulting syrup was purified by column chromatography (silica gel, elution with 7: 1 :0.1 chloroform:methanol:NH4psiH). The desired fractions were combined, concentrated, and dried in vacuo: yield 685 mg (87percent), MS: m/z 324 (M+H)+; 1HNMR (DMSOd6) delta 8.34 (s, IH, H-8), 8.15 (s, IH, H-2), 7.29 (bs, 2H, 6-NH2), 5.87 (d, IH, H-I', h\\tau = 5.4 Hz), 5.46 (bd, IH, 2'-OH), 5.22 (bd, IH, 3'-OH), 4.65 (m, IH, H-2'), 4.13 (m, IH, H-3'), 3.97-4.03 (m, IH, H-4'), 2.78 (dd, IH, 5'-CH2), 2.58-2.68 (bm, 5H, 5'-CH2, NC- CH2CH2), 2.24 (s, 3eta, N-CH3).

Reference： [1]Patent: WO2009/18541,2009,A1 .Location in patent: Page/Page column 34
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 1388 - 1407
[3]Journal of Medicinal Chemistry,1980,vol. 23,p. 121 - 127
[4]Journal of Medicinal Chemistry,1982,vol. 25,p. 550 - 556

51
[ 693-05-0 ]
[ 89-61-2 ]
[ 15950-17-1 ]
[ 81676-71-3 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

52
[ 693-05-0 ]
[ 97-09-6 ]
[ 53484-27-8 ]
[ 81676-72-4 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

53
[ 693-05-0 ]
[ 97-09-6 ]
[ 81676-72-4 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 295 - 303
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 342 - 352

54
[ 50-00-0 ]
[ 693-05-0 ]
[ 536-74-3 ]
[ 163461-53-8 ]

Reference： [1]Russian Journal of General Chemistry,2004,vol. 74,p. 1376 - 1382

55
5-chloro-pyrazine-2-carboxylic acid (2-methyl-2-phenyl-propyl)-amide [ No CAS ]
[ 693-05-0 ]
5-[(2-cyano-ethyl)-methyl-amino]-pyrazine-2-carboxylic acid (2-methyl-2-phenyl-propyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 486 - 490

56
[ 693-05-0 ]
[ 246848-23-7 ]
C₂₈H₄₀N₄O₆Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1,4-di(diphenylphosphino)-butane;tris(dibenzylideneacetone)dipalladium(0) chloroform complex; In N,N-dimethyl-formamide; at 20℃; for 12 - 36h;	Step 1: General Procedure for the Palladium Coupling Reaction Method A: [0134] To a dry, round-bottom flask, anhydrous DMF (40 mL) was added and the solvent was stirred and degassed at room temperature with two cycles of nitrogen/vacuum. Pd2(dba)3CHC13 (51.8 mg, 0.05 mmol) and DPPB (64.0 mg, 0.15 mmol) were then added. The solution was degassed with two nitrogen/vacuum cycles and aged for 20 minutes. The appropriate secondary amine (2) (1.1 mmol) was added and the mixture was again degassed under reduced pressure for 5 min. CPI 5 (590.7 mg, 1.0 mmol) was then added, the resulting mixture was again degassed with two nitrogen/vacuum cycles, and the resulting mixture was aged for 12-36h (monitored by TLC) at rt. The solvent was then removed under reduced pressure and the resulting residue was purified by flash chromatography on silica gel to produce coupled intermediate 3 in 50-98% yield.

Reference： [1]Patent: WO2005/123066,2005,A1 .Location in patent: Page/Page column 50-51; 53

57
[ 1006717-18-5 ]
[ 693-05-0 ]
[ 1006717-29-8 ]

Yield	Reaction Conditions	Operation in experiment
43%	In i-Amyl alcohol; for 5h;Heating / reflux;	Example 28 d6-3-[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-propionitrile A mixture of d6-2-chloro-4-amino-6,7-dimethoxyquinazoline (209 mg, 0.85 mmol) and N-(methylamino)-3-propanenitrile (143 mg, 1.7 mmol) in 6 mL of isoamyl alcohol was stirred at reflux under nitrogen for 5 hours. The mixture was cooled, filtered and the solid was washed several times with ethyl ether to afford the title product (120 mg, 43%). 1H NMR (300 MHz,CD3OD-d4) delta7.49 (s, 1H), 7.12 (s, 1H), 3.98 (t, J=6.6 Hz, 2H), 3.252 (s, 3H), 2.84 (t, J=6.6 Hz, 2H),; ESI-MS m/z 294 (M+H).

Reference： [1]Patent: US2008/39473,2008,A1 .Location in patent: Page/Page column 71-72

58
[ 693-05-0 ]
[ 167391-50-6 ]
[ 335411-20-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 5 - 20℃;	The reaction is performed as previously described Manoury et al, Journal of Medicinal Chemistry 1986, 29, 19-25, which is hereby incorporated by reference in its entirety. A solution of 34.8 g (0.3 mol) of tetrahydro-2-furancarboxylic acid and 30.3 g of Et3N in 250 mL of THF is added drop wise at 0 C., to 32.4 g (0.3 mol) of ethyl chloroformate. During the addition, the temperature of the mixture is kept below 5 C. The mixture is then stirred for 15 min at 5 C., and a solution of 25.2 g (0.3 mol) of 3-(methylamino)-propanenitrile in 100 mL of THF is slowly added. The mixture is then stirred for 1 hour at 5 C., allowed to warm to ambient temperature, and stirring kept overnight. The mixture is then filtered off and the solvent evaporated. The residual liquid is distilled to give the desired product, tetrahydro-N-(3-cyanopropyl)-N-methylfurancarboxamide.

Reference： [1]Patent: US2008/39473,2008,A1 .Location in patent: Page/Page column 68

59
[ 302557-28-4 ]
[ 693-05-0 ]
C₂₀H₂₆N₄O [ No CAS ]

Reference： [1]Patent: EP1184373,2002,A1 .Location in patent: Example 91

60
[ 193972-77-9 ]
[ 693-05-0 ]
C₁₂H₁₂F₂N₆OS [ No CAS ]

Reference： [1]Patent: US6362134,2002,B1 .Location in patent: Page column 403

61
[ 373354-56-4 ]
[ 693-05-0 ]
C₁₇H₁₅N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Following the procedure of Example 74 using 5,5-Dioxo-2-(4-nitrobenzoxy-carbonylamino)dibenzothiophene (Example 24) and the appropriate amine the following compounds were prepared.

Reference： [1]Patent: US2003/225097,2003,A1 .Location in patent: Page 34,37

62
[ 506-68-3 ]
[ 693-05-0 ]
[ 54434-24-1 ]

Yield	Reaction Conditions	Operation in experiment
28%	With triethylamine; In tetrahydrofuran; at -10 - 20℃; for 2h;	Cyanogen bromide (2.5 g, 0.024 mol) was dissolved in dry THF and the solution cooled to-10C in a [C02/ACETONE] bath. [N-METHYL-P-] alaninenitrile (2.2 mL, 0.024 mol), and triethylamine (3.3 mL, 0.024 mol) were added and the reaction stirred [AT-10C] for two hours. The reaction was then warmed to room temperature and left to stir overnight, under argon. The solvent was removed under reduced pressure and the residue dissolved in ether and washed with 10% aqueous citric acid and water. The organic layer was dried over sodium sulfate and the solvent removed under reduced pressure. The resulting oil (0.73 g, 28% yield) was used without further purification.

Reference： [1]Patent: WO2004/9559,2004,A2 .Location in patent: Page 32

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;acetylacetonatodicarbonylrhodium(l); 2,4-di-t-butylphenylphosphite; In toluene; at 80℃; under 20686.5 Torr; for 14h;Conversion of starting material;	A 1 gallon stainless steel autoclave was charged with poly (4-methyl-1-pentene) (76.04g, 3.5 mmol olefin functionalization, Mn of-22000), 1.5 L of toluene and 3-aminomethyl- propionitrile (20 mL, 215.6 mmol). The autoclave was pressure tested, briefly purged with N2, purged with syngas (2: 1 H2/CO), and the contents stirred under 400 psi syngas (2: 1 H2/CO) for 20 min. The reactor was heated slowly to 60 C, vented and charged with a catalyst solution comprising Rh (CO) 2 (acac) (4.42 g, 17.1 mmol) and tris-2, 4-di-t- butylphenylphosphite (23.34 g, 36.1 mmol) in 250 mL toluene via a pressurized (80 psi N2) Whitey cylinder. The reactor was then heated to 80 C, pressurized to 400 psi with syngas (2: 1 H2/CO) and stirred for 14 h. After cooling to 60 C, the reactor was purged with N2 and dumped. An equal volume of MeOH was added to induce polymer precipitation. The resulting solid was filtered and washed with acetone until the filtrate was colorless (-2 L). The filter cake was dried in a vacuum oven overnight and a sample submitted for'H NMR. Analysis of the NMR data revealed incomplete conversion of the starting material, with 65- 70% conversion to desired product. The isolated polymer mixture (vide infra), 68.75 g, was added to the same stainless steel autoclave with an additional 1.5 L of toluene and 3- aminomethyl-propionitrile (20 mL, 215.6 mmol). After purging and stirring under syngas as described above, the reaction mixture was heated to 60 C and a catalyst solution comprising Rh (CO) 2 (acac) (4.31 g, 16.7 mmol) and tris-2, 4-di-t-butylphenylphosphite (22.99 g, 35.5 mmol) in 250 mL THF was added. The reaction mixture was heated to 80 C, pressurized to 400 psi syngas (2: 1 H2/CO) and stirred for an additional 14 h. Isolation of the product as described above yielded 63.58 g of colorless powder. A sample was submitted for'H NMR. Analysis of the NMR data showed that this material was fully converted to the desired aminomethylated product.

64
[ 20850-43-5 ]
[ 693-05-0 ]
[ 327164-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia;aluminum nickel; In methanol; dichloromethane; acetonitrile;	Alternatively, compounds of formula (Y10) and derivatives thereof are prepared as follows To N-methyl-beta-alaninenitrile (50 g, mmol in acetonitrile was added piperonyl chloride (50 g, mmol). After stirring for 18 h, the solvent was removed in vacuo. The residue was dissolved in CH2Cl2, washed with aqueous carbonate, dried (MgSO4), and the solvent was removed in vacuo. The residue was dissolved in methanol saturated with ammonia (600 mL) and Raney nickel (10 g) was added. After shaking under an atmosphere of hydrogen at 20 psi for 6 h, the reaction was filtered through celite and the solvent was removed in vacuo to give 65 g of N-(1,3-benzodioxol-5-ylmethyl)-N-methyl-1,3-propanediamine.

Reference： [1]Patent: US6432947,2002,B1

65
[ 693-05-0 ]
[ 23680-84-4 ]
[ 76362-28-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With toluene-4-sulfonic acid; In butan-1-ol; for 3h;Heating / reflux;	A) Preparation of 3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]- propanenitrile (IV); A mixture of 4-amino-2-chloro-6,7-dimethoxyquinazoline (50 g, 0.208 mol), 3- methylaminopropionitrile (35.07 g, 0.416 mol) and jp-toluenesulphonic acid (39.71 g, 0.208 mol) was heated to reflux in 1-butanol (350 ml) for 3 hr. The reaction mass was concentrated at 70-80C under reduced pressure. The resulting concentrated mass was stirred with aqueous ethanol (50% v/v, 250 ml) and pH of the mixture was adjusted to 10.0 to 10.5. Thereafter, the precipitate was filtered and dried at 60-65C under vacuum <n="9"/>to obtain 3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]-propanenitrile. Yield: 55.0 g (92% of theory)
78.0%	In i-Amyl alcohol; at 135 - 140℃; for 4h;	EXAMPLE 1; [0092] Preparation of N-(4-amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2- cyanoethyl amine[0093] 4-amino-2-chloro-6,7-dimethoxyquinazoline (200.0 g) and methylaminopropionitrile (84.20 g) were charged in isoamyl alcohol (1400.0 ml) and heated to reflux a temperature ranging from about 135C to about 1400C for 4 hours. Reaction completion is checked by Thin Layer Chromatography ("TLC"). After completion of the reaction as determined by TLC, mass is cooled, filtered and dried. The dried material is then crystallized form aqueous ethanol to get N-(4-amino-6, 7- dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethyl amine (185.0 g, 78.0% yield). HPLC purity > 96 %
	In i-Amyl alcohol;	EXAMPLE II N1 -(4-Amino-6,7-dimethoxyquinazol-2-yl)-N1 -methyl-N2 -(tetrahydrofuroyl-2)-propylenediamine and its monohydrochloride. STR11 A mixture of 14.4 g (0.06 mol) of 4-amino-2-chloro-6,7-dimethoxyquinazoline and 10 g (0.12 mol) of 3-methylaminopropionitrile in 100 ml of isoamyl alcohol is heated at reflux temperature for 5 hours. After cooling the precipitate is collected and washed repeatedly with hot ethanol. The N-(4-amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethylamine thus obtained melts at about 270 C.

	In N,N-dimethyl acetamide; at 125 - 135℃; for 2h;	Example- 1: N-(4-amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethylamine (II) A mixture of 4-Amino-2-chloro-6,7-dimethoxyquinazoline (500 gm) and 3- (methylamino)propionitrile (265 gm) in N,N-dimethylacetamide (1.0 L ) was heated at 125 to 1350C for two hours. The reaction mixture was cooled to ambient temperature and the separated solid was filtered. The wet solid so obtained was washed with N9N- dimethylacetamide and dried to get the title compound. Yield: 465 gm
	In N,N-dimethyl-formamide; at 120 - 125℃; for 1.5h;	Example-1: - Preparation of N-(4-amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2- cyanoethylamineA mixture of 475.0 g (1.0 mol) of 4-amino-2-chloro-6,7-dimethoxyquinazoline was taken in 832 niL DMF in RBF and heated it to 1200C to 1250C. 208 g (1.25 mole) of 3-methylaminopropionitrile was added within an hour. The reaction mixture was maintained for 30 minutes and cooled to room temperature. The reaction mixture was poured in aq. ammonia (1664.0 mL of ammonium solution in 6656.0 mL of water) and stirred for 2 hours at room temperature. The N-(4-mino-6,7-dimethoxyqumazol-2-yl)- N-methyl-2-cyanoethylamine thus obtained melts at about 27O0C, was filtered, washed with water and dried at 5O0C to 550C to give 653.2 g of N-(4-mino-6,7- dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethylamine.
	In N,N-dimethyl acetamide; at 80 - 85℃; for 12 - 15h;Product distribution / selectivity;	Example-1; A mixture of 10 gm (0.04174 moles) 2-chloro-4-amino-6,7-dimethoxy quinazoline, 7.0 gm 3-methylaminopropionitirle (0.83 moles) and 30 ml N,N-dimethylacetamide was heated at 80-85 0C for 12-15 hrs. The progress of reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled and water was added to it. The reaction mixture was chilled for 1-2 hr and filtered off. The solid mass was dried to obtain 10.4 gm of N-(4- amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethylamine. HPLC purity. >98%
	In 4-methyl-2-pentanone; for 48h;Heating / reflux;Product distribution / selectivity;	Example -2; A mixture of 10 gm (0.04174 moles) 2-chloro-4-amino-6,7-dimethoxy quinazoline, 7.0 gm 3-methylaminopropionitirle (0.83 moles) and 50 ml methylisobutylketone is refluxed for 48 hrs. The progress of reaction was monitored by TLC. After completion of the reaction, the reaction mixture is cooled to O0C and maintained for 1-2 hrs. The reaction mixture is filtered off and washed with methylisobutylketone. Further it is dried to obtained 10.2 gm of N-(4- amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethylamine. HPLC purity: >98%

Reference： [1]Patent: WO2007/74364,2007,A1 .Location in patent: Page/Page column 7-8
[2]Patent: WO2006/90268,2006,A2 .Location in patent: Page/Page column 27
[3]Patent: US4315007,1982,A
[4]Patent: WO2007/69050,2007,A2 .Location in patent: Page/Page column 8
[5]Patent: WO2008/114272,2008,A2 .Location in patent: Page/Page column 8
[6]Patent: WO2009/1369,2008,A1 .Location in patent: Page/Page column 7
[7]Patent: WO2009/1369,2008,A1 .Location in patent: Page/Page column 7

66
(E)-[4-(4-bromo-but-2-enyloxy)-phenyl]-(4-bromo-phenyl)-methanone [ No CAS ]
[ 693-05-0 ]
(E)-3-[[4-[4-(4-bromo-benzoyl)-phenoxy]-but-2-enyl]-methyl-amino]-propionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		k) from (E)-[4-(4-bromo-but-2-enyloxy)-phenyl]-(4-bromo-phenyl)-methanone and 3-methylaminopropionitrile there is obtained (E)-3-[[4-[4-(4-bromo-benzoyl)-phenoxy]-but-2-enyl]-methyl-amino]-propionitrile which is converted into the fumarate, MS: m/e 413 (M+H+, 1Br),

Reference： [1]Patent: US6034275,2000,A

67
[ 693-05-0 ]
[ 2937-50-0 ]
[ 158773-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;	Example 6 Preparation of O-allyl-N-(2-cyanoethyl)-N-methylcarbamate The procedure of example 1 was used except for 55.5 g (2-cyanoethyl)methylamine, 80 g allylchloroformate and 26.55 g sodium hydroxide. The amounts of water and methylene chloride were adjusted accordingly. Boiling point is 125 C. at 0.05 torr. 1 H NMR is consistent with the structure.

Reference： [1]Patent: US5374755,1994,A

68
[ 149169-51-7 ]
[ 693-05-0 ]
[ 149169-59-5 ]
[ 149169-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; toluene;	Application Example 5 3-Ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(b-cyanoethyl)amino]quinoline is prepared in the following manner: 19.08 g of sodium carbonate are added to a solution of 16.3 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline, prepared as described in Application Example 1, and 10 g of N-methyl-N-(b-cyanoethyl)amine in 160 cm3 of toluene. The suspension obtained is heated to reflux and then stirred for 4 hours at this temperature. The reaction mixture is then cooled to approximately 20 C. and thereafter washed with 3 times 50 cm3 of water. The organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50 C. 19.17 g of 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(b-cyanoethyl)amino]quinoline are obtained in the form of an oil, which is used without further purification for the subsequent steps. 3-Cyano-7,8-difluoro-1-methyl-4-oxo-1,2,3,4-tetrahydro-benzo[b][1,8]naphthyridine is prepared in the following manner:
	With sodium carbonate; In water; toluene;	EXAMPLE 4 3-Ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(beta-cyanoethyl)amino]quinoline is prepared in the following manner: 19.08 g of sodium carbonate are added to a solution of 16.3 g of 2-chloro-3-ethoxycarbonyl-6,7-difluoroquinoline and 10 g of N-methyl-N-(beta-cyanoethyl)amine in 160 cm3 of toluene. The suspension obtained is heated to reflux and then stirred for 4 hours at this temperature. The reaction mixture is then cooled to approximately 20 C. and thereafter washed with 3 times 50 cm3 of water. The organic phase is concentrated to dryness under reduced pressure (20 kPa) at approximately 50 C. 19.17 g of 3-ethoxycarbonyl-6,7-difluoro-2-[N-methyl-N-(beta-cyanoethyl)amino]quinoline are obtained in the form of an oil, which is used without further purification for the subsequent steps. 3-Cyano-7,8-difluoro-1-methyl-4-oxo-1,2,3,4-tetrahydrobenzo[b][1,8]naphthyridine is prepared in the following manner:

Reference： [1]Patent: US5442070,1995,A
[2]Patent: US5484921,1996,A

69
[ 693-05-0 ]
[ 75-65-0 ]
[ 5332-06-9 ]
[ 1859-29-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	STEP A: 3-methyl-3-aza-1,6-dicyano hexane 75 g of 4-bromo-butyronitrile were added to a stirred mixture at 20 C. of 42 g of methylamino propionitrile, 325 ml of tert-butyl alcohol and 70 g of potassium carbonate and the mixture was refluxed with stirring for 2 hours, then for 16 hours at ambient temperature. The insoluble part was filtered off and the filtrate was concentrated. The 96 g of residue were chromatographed on silica (eluant: chloroform-acetone-cyclohexane (1-1-1) to obtain 54 g of the expected product.

Reference： [1]Patent: US5064861,1991,A

70
[ 693-05-0 ]
[ 53059-74-8 ]
1-(1,3-dithiol-2-ylidene)-N-methyl-N-(2-cyanoethyl)ammonium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In tetrahydrofuran;	EXAMPLE 13 To 30 ml of tetrahydrofuran, 0.8 g of N-methyl-(2-cyanoethyl)amine was dissolved, and 2.0 g of 2-methylthio-1,3-dithiolium iodide was gradually added thereto under stirring at room temperature. The mixture was stirred at room temperature for 1 hour, and then the precipitated crystals were collected by filtration and recrystallized from acetone-ethyl ether, whereby 1.8 g (yield: 80%) of 1-(1,3-dithiol-2-ylidene)-N-methyl-N-(2-cyanoethyl)ammonium iodide (Compound No. 4) was obtained as crystals having a melting point of 203 C. IR numaxKBr cm-1: 3070, 2250, 1563, 1520, 1405, 1235, 1112, 830. NMR(D2 O)delta: 3.13(2H, t J=7 Hz), 3.55(3H, s), 4.21(2H, t J=7 Hz), 7.62(2H, s).

Reference： [1]Patent: US4737494,1988,A

71
[ 693-05-0 ]
[ 93-97-0 ]
[ 23873-66-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydroxide; In dichloromethane;	(a) 3-(N-benzoyl-N-methyl-amino)-propionitrile 35.2 g (0.42 mol) of N-methyl-3-amino-propionitrile (prepared as described in J. Chem. Soc. 1945, 399-402) in 100 ml of methylene chloride are added to a solution of 94 g (0.42 mol) of benzoic anhydride in 100 ml of the same solvent. The temperature rises to 50 C. since the reaction is exothermic. After stirring for about 11/2 hours, the mixture is treated with an iced solution of sodium hydroxide and then washed with water and the organic phase is dried over Na2 SO4. The solvent is evaporated under reduced pressure. 68 g of nitrile (yield 87%) are obtained.

Reference： [1]Patent: US4341893,1982,A

72
[ 65287-34-5 ]
[ 693-05-0 ]
[ 113969-53-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethyl acetate; acetonitrile;	PREPARATION EXAMPLE 1 Preparation of N-(2-cyanoethyl)-N-methyl-2-chloroisonicotinamide (No. 2) 2 g (0.0136 mol) of 2-chloroisonicotinoyl chloride was added dropwise to a solution comprising 1.2 g (0.01136 mol) of N-methyl-N-(2-cyanoethyl)amine, 1.9 ml (0.0136 mol) of triethylamine and 30 ml of acetonitrile under cooling at 5 to 10 C. The mixture was stirred at room temperature for 2 h and then poured into water. Ethyl acetate was added thereto to conduct extraction. The organic layer was washed with a saturated aqueous common salt solution and dried over anhydrous sodium sulfate. The solvent was distilled off and the resulting crude product was purified according to silica gel column chromatography to obtain 2.1 g (yield: 83.2%) of a light yellow oily product having nD25 of 1.5490.

Reference： [1]Patent: US4804762,1989,A

73
[ 693-05-0 ]
[ 42432-30-4 ]
[ 25316-59-0 ]
3-[N-(p-chlorocinnamyl)-methylamino]-propionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane;	(a) A solution of 116 g of p-chlorocinnamyl bromide in 500 ml of methylene chloride is added dropwise with stirring to a mixture of 42 g of 3-methylamino-propionitrile and 8.9 g of benzyl-tri-(n-butyl)ammonium bromide in 1 liter of methylene chloride and 500 ml of 2 N sodium hydroxide solution at room temperature and under a nitrogen atmosphere, and the emulsion stirred for 65 hours at room temperature. The organic phase is separated, washed with water, dried over sodium sulphate and evaporated to yield 3-[N-(p-chlorocinnamyl)-methylamino]-propionitrile. M.P. 143 [hydrogen oxalate form]

Reference： [1]Patent: US4164583,1979,A

74
[ 693-05-0 ]
[ 110-53-2 ]
3-(N-methyl-N-pentylamino)propionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 40℃; for 9 - 10h;	Example 1; Preparation of 3-(N-Methyl-N-pentylamino) propionitrile; Into a 3L, three-necked RB flask were charged 1.5L of DMF, 300g of 3 -N- methylaminopropionitrile, and 30Og of potassium carbonate at RT. Pentyl bromide (60Og) was slowly added to the reaction mass keeping the internal temperature below 40C. After the addition reaction was maintained at same temperature for 9-1 Ohr. Sample was taken out from the reaction mass and checked for the presence of 3-(N- methylamino)propionitrile by GC. Reaction was found to be over by GC.Into a 2OL flask water (12L) was taken and quenched the reaction mass into the water below 25C. The reaction mass was stirred for lhr and separated the organic layer. The aqueous layer was extracted with 700ml of toluene. Combined the toluene layer with organic layer and washed with 2 x 1.5L of water. Toluene was distilled off from the organic layer below 70C. The residue containing more than 85% of required product was fractionally distilled at 1400C under vaccum to get the title compound (29Og) as colorless liquid. GC purity of this compound showed more than 99%. IR (neat): 2955, 2932, 2860, 2799, 2249, 1464, 1426, 1378,1334, 1254, 1195, 1158, 1134, 1098, 1051, 935, 830, 772, and 729cm"1. 1H-NMR (300MHz, CDCl3): 2.72 (t, J = 7.0Hz, 2H, - CH2CH2CN); 2.47 (t, J = 6.6Hz, 2H, -CH2CN); 2.38 (t, J = 6.9Hz, 2H, -NCH2); 2.27 (s, 3H5 NCH3); 1.24-1.69 (m, 6H, -CH2CH2CH2-); 0.89-0.93 (m, 3H, -CH3).

Reference： [1]Patent: WO2007/13097,2007,A1 .Location in patent: Page/Page column 7

75
[ 4548-45-2 ]
[ 693-05-0 ]
[ 109752-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3.5h;	Preparation of 3-[methyl-(5-nitro-pyridin-2-yl)-amino]-propionitrile 2-Chloro-5-nitropyridine (158 mg, 1 mmol), 3-methylamino-propionitrile (84 mg, 1 mmol), and finely ground potassium carbonate (414 mg, 3 mmol) were heated to 80 C. in 10 mL anhydrous DMF for 3.5 hrs. The mixture was diluted with EtOAc, extracted with H2O and dried over MgSO4. The EtOAc layer was filtered, evaporated to dryness. ES-MS calcd for C9H10N4O2 (m/e) 206.21, obsd 207.1 (M+H).

Reference： [1]Patent: US2007/123504,2007,A1 .Location in patent: Page/Page column 34

76
[ 132900-51-7 ]
[ 693-05-0 ]
[ 76362-28-2 ]

Yield	Reaction Conditions	Operation in experiment
	In sulfolane; at 130℃; for 5h;	EXAMPLE 1 Preparation of N-(4-AMINO-6,7-DIMETHOZYQUINAZOL-2-YL)-N-METHYL-2-CYANOETHYLAMINE To 100 g (0.362 moles) of 4-amino-2-chloro-6,7-dimethoxyquinazoline hydrochloride, was added 34.08 g (0.405 moles) of 3-methylaminopropionitrile and 700 ml of sulfolane, and stirred for 5 hours under reflux temperature 130 C. The reaction mass was cooled to room temperature, filtered the crystallized material and dried under vacuum for an hour. The material was washed with 400 ml of isopropanol in a 3-lit Torson beaker, filtered and vacuum dried for an hour. The material was further dried at 45 C.-50 C. for 6 hours. The crude material was then added to 4120 ml of water, stirred for 30 minutes at room temperature and the pH adjusted between 7.25-7.50. The reaction solution was cooled to 10 C. and stirred for an hour at the same temperature. The crystalline material was filtered, washed twice with 200 ml of water and dried to obtain 95 g of N-(4-amino-6,7-dimethoxyquinazol-2-yl)-N-methyl-2-cyanoethylamine. HPLC Purity: >98%

Reference： [1]Patent: US2007/105880,2007,A1 .Location in patent: Page/Page column 6

77
[ 439578-86-6 ]
[ 693-05-0 ]
[ 1012060-85-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 634 - 639

78
[ 764710-89-6 ]
[ 693-05-0 ]
[ 109505-75-1 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 2924 - 2929

79
(η(5)-pentadienyl)Fe(CO)3(+) [ No CAS ]
[ 693-05-0 ]
[ 166832-71-9 ]

Reference： [1]Organometallics,1995,vol. 14,p. 3396 - 3407

80
[ 630107-80-1 ]
[ 693-05-0 ]
C₂₄H₂₄N₈O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2652 - 2657

81
[ 693-05-0 ]
[ 80745-07-9 ]
[ 1073697-24-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine; In tetrahydrofuran; at 20℃; for 16h;	Synthesis of the carbamates; Synthesis of phenyl 3-(4-methoxy-N,2,3,6-tetramethylphenylsulfonamido)-propylcarbamate V1; N-(2-Cyanoethyl)-4-methoxy-N,2,3,6-tetramethylbenzenesulfonamide; 4-Methoxy-2,3,6-trimethylbenzenesulfonyl chloride (5.00 g, 20 mmol) was added at room temperature to a solution of 3-methylaminopropionitrile (1.50 g, 18.3 mmol) and triethylamine (5.50 g, 55 mmol) in THF (30 ml), and stirring was carried out for 16 h. Ethyl acetate (50 ml) was then added to the reaction mixture, and washing with sodium hydrogen carbonate solution (3×50 ml) was carried out. The organic phase was dried over sodium sulfate and concentrated in vacuo.Yield: 4.92 g (91%)1H-NMR (DMSO-d6): 2.09 (s, 3H); 2.44 (s, 3H); 2.59 (s, 3H); 2.68 (s, 3H); 2.76 (t, 2H); 3.30 (t, 2H); 3.84 (s, 3H); 6.87 (s, 1H).

Reference： [1]Patent: US2008/312231,2008,A1 .Location in patent: Page/Page column 43

82
[ 693-05-0 ]
[ 55525-63-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; water; at 95℃; for 20h;	3-(methylamino)propanenitrile (10 mL, 105.7 mmol) was treated with 200 mL of aqueous IN NaOH and stirred at 95 0C for 20 h. After the mixture was cooled to room temperature a solution of BoC2O (34.6 g, 158.5 mmol) in 200 mL of THF was added, and the mixture was stirred at room temperature for 24 h before being washed with Et2O (2 x 200 mL) and CH2Cl2 (2 x 200 mL). The aqueous layer was cooled to 0 C, acidified to pH 4 by the addition of aqueous 7N HCl, and extracted with CH2Cl2 (2 x 150 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to give JV-{ [(1 , 1 - dimethylethyl)oxy]carbonyl}-N-methyl-beta-alanine as a colorless oil (17.53 g, 80 %).

Reference： [1]Patent: WO2008/156831,2008,A2 .Location in patent: Page/Page column 73

83
[ 19836-78-3 ]
[ 693-05-0 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 4857 - 4858

84
[ 67-56-1 ]
[ 693-05-0 ]
methyl 3-(N-methylamino)propionate hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2623 - 2627

85
[ 693-05-0 ]
[ 170235-26-4 ]
methyl 2-((2-cyanoethyl)(methyl)amino)thiazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 16.083h;Sealed tube; Inert atmosphere;	In a sealable tube, a solution of <strong>[170235-26-4]methyl 2-bromothiazole-4-carboxylate</strong> (0.500 g, 2.252 mmol) and 3-(methylamino)propanenitrile (0.176 mL, 1.876 mmol) in dioxane (8 mL) was treated with cesium carbonate (0.611 g, 1.876 mmol), palladium(II) acetate (0.021 g, 0.094 mmol) and Xantphos (0.065 g, 0.113 mmol). The system was purged with nitrogen for 5 min and then the tube was sealed and the mixture heated at 100 C for 16 h. The cooled reaction mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue obtained was chromatographed on silica gel (ISCO, elution gradient of methanol in dichloromethane) to give 0.300 g (59%) of the title compound. LC (Method B): 1.927 min. LCMS (APCI): calcd for C9H12N3O2S [M+H]+ m/z 226.07; found 226.0.

Reference： [1]Patent: WO2013/163279,2013,A1 .Location in patent: Paragraph 00301

86
[ 693-05-0 ]
[ 5274-70-4 ]
3-((2-hydroxy-3-nitrobenzyl)amino)propanenitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3521 - 3525

87
[ 3476-89-9 ]
[ 693-05-0 ]
3,3'-(quinoxaline-2,6-diylbis(methylazanediyl))dipropanenitrile [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 15858 - 15862

88
[ 693-05-0 ]
[ 102391-98-0 ]
[ 530-62-1 ]
N-(2-cyanoethyl)-4-(4-fluorobenzoyl)-N-methylpiperazine-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.64 g		1,1?-carbonyldiimidazole (2.45 g, 70 wt%, 10.6 mmol) was added to a solution of 3- methylaminopropionitrile (890 mg, 10.6 mmol) in 25 mL dichloromethane. The solution was stirred under reux for 1 h, cooled to rt and amide 4.31 (1.80 g, 8.65 mmol) and toluene was added and the mixture was heated for 3 d at 80C. The mixture was rotary evaporated and 100 mL toluene was added to the residue. The mixture was washed with 2 x 25 mL water, then dried and rotary evaporated to give the product (2.64 g) which was used as such in the next step. 1H-NMR (CDCl3): 6 7.4 (m, 2H), 7.1 (m, 2H), 3.2- 3.8 (broad m) and 3.45 (t) (10H), 3.0 (s, 3H), 2.65 (t, 2H).

Reference： [1]Patent: WO2019/212356,2019,A1 .Location in patent: Page/Page column 201; 202

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Code	Phrase
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Prevention
Code	Phrase
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Code	Phrase
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P321
P322
P330	Rinse mouth.
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P378
P380	Evacuate area.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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P420	Store away from other materials.
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P411 + P235	Keep cool.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H272	May intensify fire; oxidizer
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H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 693-05-0 ] {[proInfo.proName]}

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[ 693-05-0 ] Synthesis Path-Upstream 1~5

[ 693-05-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 693-05-0 ]

Aliphatic Chain Hydrocarbons

Amines

Nitriles

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[ 693-05-0 ]