149765-15-1|N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide| Ambeed

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Quality Control of [ 149765-15-1 ] Purity: 95% SDS Specification

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Product Details of [ 149765-15-1 ]

CAS No. :	149765-15-1
Formula :	C₁₁H₁₃ClN₄O
M.W :	252.70
SMILES Code :	ClC1=NC(=NC2=C1C=C[NH]2)NC(C(C)(C)C)=O
MDL No. :	MFCD11109809
InChI Key :	HNBVXLCVUIJCSK-UHFFFAOYSA-N
Pubchem ID :	11425285

Safety of [ 149765-15-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 149765-15-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	9
Fraction Csp3	0.36
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	67.37
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	70.67 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.15
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.41
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.22
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.36
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.2
Solubility	0.159 mg/ml ; 0.00063 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.67
Solubility	0.0539 mg/ml ; 0.000213 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.37
Solubility	0.0108 mg/ml ; 0.0000427 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.04 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.07

Application In Synthesis of [ 149765-15-1 ]

* 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.

Downstream synthetic route of [ 149765-15-1 ]

[ 149765-15-1 ] Synthesis Path-Downstream 1~35

1
[ 3282-30-2 ]
[ 84955-31-7 ]
[ 149765-15-1 ]

Yield	Reaction Conditions	Operation in experiment
22 g (83%)	In pyridine; water;	EXAMPLE 2 4-Chloro-5-iodo-2-pivaloylamino-pyrrolo[2,3-d]pyrimidine (I) STR3 A solution of 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine (20 g, 118 mmol) and pivaloyl chloride (14.3 g, 118 mmol) in pyridine (150 mL) was stirred for 18 hours at ambient temperature. The resulting dark red solution was evaporated to an amber solid which was co-evaporated with water (20 mL, 3*). The resulting solid was filtered, washed with cold water and then dried over KOH in vacuo to yield 22 g (83%) of 2-pivaloylamino-4-chloro-pyrrolo[2,3-d]pyrimidine as a reddish solid. 1 H-NMR (DMSO-d6): delta 12.35 (bs, 1, N (7)-H); 10.07 (s,1, N (2)-H); 7.56 (m,1, H-6); 6.58 (m,1, H-5); 1.24 (s, 9, pivaloyl methyls).
	With pyridine; at 20℃; for 16h;Inert atmosphere;	4-Chloro-2-trimethylacetamido-pyrrolor2.3-^lpyrimidine (9a).To a stirring solution of 2-amino-4-chloro-py?Olo[2,3-fiT]pyrirnidine (7.3 g, 43.61 mmol) in anhydrous pyridine (120 mL) was added pivaloyl chloride (18.7 mL, 152.63 mmol). The reaction was stirred at RT under nitrogen for 16 h and quenched with MeOH (50 mL). The solvents were then removed in vacuo, and the residue was co-evaporated with toluene (100 mL). The resulting residue was dissolved in EtOAc (150 mL) and washed with 0.1 M HCl (3x75 mL). The organic layer was dried (MgSO4) and evaporated. The crude material was resolved by silica chromatography (30% EtOAc/hexane) to yield 9a (12.2 g) as a white crystalline solid. 1H-NMR (DMSO-): 1.2 (9H, s), 6.5 (IH, d, Ji = 4 Hz), 7.5 (IH, d, Ji = 4 Hz), 10.1 (IH, s), 12.3 (IH, s).

References: [1]Chemistry - A European Journal,2020.
[2]Synthesis,2004,p. 1203 - 1210.
[3]Heterocycles,1993,vol. 35,p. 825 - 841.
[4]Angewandte Chemie - International Edition,2007,vol. 46,p. 2325 - 2327.
[5]Nucleosides and Nucleotides,1997,vol. 16,p. 941 - 944.
[6]Patent: US6093807,2000,A .
[7]Patent: WO2010/110775,2010,A1 .Location in patent: Page/Page column 33.
[8]Chemistry and biodiversity,2019,vol. 16.

2
[ 149765-15-1 ]
[ 149765-16-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-iodo-succinimide; In tetrahydrofuran; at 20℃; for 0.666667h;	Step 4. N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide A solution of <strong>[149765-15-1]N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide</strong> (101 g, 0.40 mol) in anhydrous THF (2 L) was treated with N-iodosuccinimide (98.9 g, 0.44 mol, 1.1 eq.) under N2 atmosphere at rt for 40 min. The solvent was evaporated, and the residue was taken up in CH2Cl2 (1.5 L), and washed with Na2SO3 (500 mL3) and brine (300 mL3). Evaporated and recrystallizion from MeOH gave the title product as a white powder (122 g, 81% yield, HPLC purity: 98.2%). tR: 6.19 min. 1H-NMR (DMSO-d6) delta 12.65 (br.s, 1H), 10.11 (br. s, 1H), 7.76 (d, 1H), 1.24 (s, 9H).
30.5 g (94%)	With N-iodo-succinimide; In N,N-dimethyl-formamide;	A solution of the <strong>[149765-15-1]2-pivaloylamino-4-chloro-pyrrolo[2,3-d]pyrimidine</strong> (21.5 g, 85 mmol) and N-iodosuccinimide (19.12 g, 85 mmol) in DMF (150 mL) was stirred at ambient temperature for 18 hr. The red solution was evaporated to an amber residue which upon trituration with cold water gave a yellow solid. The solid was collected by filtration, the filter cake was washed with cold water and then dried in vacuo to yield 30.5 g (94%) of the title compound. 1 H-NMR (DMSO-d6): delta 12.72 (s,1, N (7)-H); 10.14 (s,1, N(2)-H); 7.78 (d,1, H-6); 1.24 (s, 9, pivaloyl methyls). mp 218-220 C.
	With N-iodo-succinimide; In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere;	4-Chloro-5-iodo-2-trimethylacetamido-pyrrolor2.3-(flpyrimidine (9b).4-Chloro-2-trimethylacetamido-pyrrolo[2,3-rf]pyrimidine (9a, 10.9 g, 43.24 mmol) was dissolved in anhydrous THF (120 mL) under nitrogen. After the addition of LambdaModosuccinimide (10.7 g, 47.56 mmol), the mixture was stirred at RT for 1 h. The solvent was then removed in vacuo. The residue dissolved in EtOAc (100 mL) and washed with 1 M sodium thiosulfate (3x100 mL). Column chromatography purification (2% MeOH in DCM, isocratic ) yielded 9b (12.9 g). 1H-NMR (DMSO-rfbeta): 1.2 (9H, s), 7.8 (IH, d, Ji = 4 Hz), 10.1 (IH, s), 12.7 (IH, s).

References: [1]Chemistry - A European Journal,2020.
[2]Synthesis,2004,p. 1203 - 1210.
[3]Heterocycles,1993,vol. 35,p. 825 - 841.
[4]Angewandte Chemie - International Edition,2007,vol. 46,p. 2325 - 2327.
[5]Patent: US2006/223797,2006,A1 .Location in patent: Page/Page column 83-84.
[6]Journal of Medicinal Chemistry,2012,vol. 55,p. 7786 - 7795.
[7]Nucleosides and Nucleotides,1997,vol. 16,p. 941 - 944.
[8]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.
[9]Patent: US6093807,2000,A .
[10]Patent: WO2010/110775,2010,A1 .Location in patent: Page/Page column 33.

3
[ 7486-35-3 ]
[ 149765-15-1 ]
[ 502160-37-4 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

4
[ 137281-08-4 ]
[ 149765-15-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-benzyl-N,N,N-triethylammonium chloride; N,N-dimethyl-aniline; trichlorophosphate; In acetonitrile; for 0.666667 - 1h;Heating / reflux;	Step 3. N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide A mixture of 2,2-dimethyl-N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-propionamide (210 g, 0.90 mol), POCl3 (828 g, 5.40 mol, 503 mL, 6.0 eq), benzyltriethylammonium chloride (411 g, 1.80 mol), N,N-dimethylaniline (220 g, 231 mL, 1.80 mol), and acetonitrile (2.0 L) was heated to reflux for 40-60 min, monitoring with HPLC. The solvent was evaporated on a rotary evaporator, and the residue was carefully (caution: exothermic and corrosive) and slowly added to ice water (16 L). The pH was adjsuted to 7 with solid NaOH, and the resulting precipitate was collected by filtration. Drying afforded the title compound (159 g, 70% yield 70%, HPLC purity 100%). tR: 5.37 min. 1H-NMR (DMSO-d6) delta 12.35 (br. s, 1H), 10.06 (br. s, 1H), 7.54 (q, 1H), 6.52 (q, 1H), 1.25 (s, 9H).

References: [1]Patent: US2006/223797,2006,A1 .Location in patent: Page/Page column 83-84.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7786 - 7795.
[3]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

5
[ 149765-15-1 ]
[ 737792-27-7 ]

References: [1]Synthesis,2004,p. 1203 - 1210.

6
[ 149765-15-1 ]
[ 737792-28-8 ]

References: [1]Synthesis,2004,p. 1203 - 1210.

7
[ 149765-15-1 ]
[ 909101-45-7 ]

Yield	Reaction Conditions	Operation in experiment
30%	With acetic acid; Selectfluor; In acetonitrile; at 50℃; for 0.5h;Inert atmosphere;	4-Chloro-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine 34 (150 mg, 0.59 mmol) and selectfluor (320 mg, 0.90 mmol) were placed in a round-bottom flask, followed by the addition of anhydrous MeCN (6 mL) and AcOH (0.6 mL). The mixture was then heated at 50 00 for 30 mm under N2. The mixture was then cooled by ice-water and diluted with CH2CI2 (50 mL). The organic layer was washed with sat. NaHCO3 (50 mL). The inorganic layer was separated and extracted with CH2CI2 (2 x 20 ml). The combined organic layers were dried with Na2SO4, filtered and concentrated under reduce pressure. The residue was then purified by column chromatography on silica gel (gradient DCM/MeOH, 200:1) to give 35 (48 mg, 30%) as a colorless foam. 1H NMR (300 MHz, CDCI3): 611.79 (s, 1H, NHOO), 8.25 (s, 1H, H-6), 1.39 (s, 9H, (0H3)30); 130 NMR (75 MHz, 0D013): 176.5 (NHCO), 151.3 (0-2), 150.8 (0-4), 147.8 (0-7a), 141.4 (d, 1JC,F = 248.8 Hz, 0-5), 111.2 (d, 2JC,F = 26.0 Hz, 0-6), 103.6 (d, 2JC,F = 14.9 Hz, C-4a), 40.5 (C(0H3)3), 27.7 (C(CH3)3).

References: [1]Synthesis,2006,p. 2005 - 2012.
[2]Patent: WO2018/55071,2018,A1 .Location in patent: Page/Page column 52; 55.
[3]Chemistry and biodiversity,2019,vol. 16.

8
[ 149765-15-1 ]
2-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-5-fluoro-4H-pyrrolo[2,3-d]pyrimidin-4-one [ No CAS ]

References: [1]Synthesis,2006,p. 2005 - 2012.

9
[ 149765-15-1 ]
[ 909101-51-5 ]

References: [1]Synthesis,2006,p. 2005 - 2012.

10
[ 149765-15-1 ]
[ 1067137-28-3 ]

References: [1]Synthesis,2006,p. 2005 - 2012.

11
[ 149765-15-1 ]
[ 199938-75-5 ]

References: [1]Synthesis,2004,p. 1203 - 1210.
[2]Nucleosides and Nucleotides,1997,vol. 16,p. 941 - 944.

12
[ 149765-15-1 ]
[ 199938-73-3 ]

References: [1]Synthesis,2004,p. 1203 - 1210.
[2]Nucleosides and Nucleotides,1997,vol. 16,p. 941 - 944.

13
[ 149765-15-1 ]
[ 737792-24-4 ]

References: [1]Synthesis,2004,p. 1203 - 1210.

14
[ 149765-15-1 ]
[ 737792-34-6 ]

References: [1]Synthesis,2004,p. 1203 - 1210.

15
[ 149765-15-1 ]
[ 737792-33-5 ]

References: [1]Synthesis,2004,p. 1203 - 1210.

16
[ 149765-15-1 ]
[ 201528-75-8 ]

References: [1]Synthesis,2004,p. 1203 - 1210.

17
[ 149765-15-1 ]
[ 737792-29-9 ]

References: [1]Synthesis,2004,p. 1203 - 1210.

18
[ 149765-15-1 ]
[ 737792-31-3 ]

References: [1]Synthesis,2004,p. 1203 - 1210.

19
[ 149765-15-1 ]
[ 149765-17-3 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.
[2]Heterocycles,1993,vol. 35,p. 825 - 841.

20
[ 149765-15-1 ]
[ 502160-38-5 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

21
[ 149765-15-1 ]
[ 502160-39-6 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

22
[ 149765-15-1 ]
[ 502160-45-4 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

23
[ 149765-15-1 ]
[ 502160-43-2 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

24
[ 149765-15-1 ]
2-{4-[2-(2-amino-4-ethyl-7<i>H</i>-pyrrolo[2,3-<i>d</i>]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

25
[ 149765-15-1 ]
[ 502160-46-5 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

26
[ 149765-15-1 ]
[ 502160-41-0 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 591 - 600.

27
[ 149765-15-1 ]
[ 213823-29-1 ]