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Structure of 255735-88-7

Chemical Structure| 255735-88-7

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Product Details of [ 255735-88-7 ]

CAS No. :255735-88-7
Formula : C8H18N2O2
M.W : 174.24
SMILES Code : O=C(OC(C)(C)C)NCC(N)C
MDL No. :MFCD09788609

Safety of [ 255735-88-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H319
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 255735-88-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.88
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 47.79
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

64.35 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.21
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.42
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.86
Log Po/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.

0.63
Log Po/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

-0.03
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.82

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.85
Solubility 24.3 mg/ml ; 0.14 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.34
Solubility 7.99 mg/ml ; 0.0459 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-1.31
Solubility 8.55 mg/ml ; 0.0491 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

No
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

No
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.

-7.06 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

1.0
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<1.0
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)

2.54

Application In Synthesis of [ 255735-88-7 ]

* 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 [ 255735-88-7 ]

[ 255735-88-7 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 50-00-0 ]
  • [ 20924-05-4 ]
  • [ 1930-94-5 ]
  • [ 255735-88-7 ]
  • rac-2-[(2-tert-butyloxycarbonyl-amino-1-methyl-ethyl)-thyminacetyl-amino]-acetic acid-4-methoxy-2-nitro-phenylamide [ No CAS ]
  • 2
  • [ 13303-10-1 ]
  • [ 78-90-0 ]
  • [ 255735-88-7 ]
  • 4
  • [ 2495-35-4 ]
  • [ 255735-88-7 ]
  • [ 851017-82-8 ]
  • 5
  • [ 86-98-6 ]
  • [ 255735-88-7 ]
  • [2-(7-chloroquinolin-4-ylamino)propyl]carbamic acid tert-butyl ester [ No CAS ]
  • 6
  • [ 255735-88-7 ]
  • [ 851017-83-9 ]
  • 7
  • [ 255735-88-7 ]
  • [ 851017-84-0 ]
  • 8
  • {(1S)-1-[2-(1-[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}piperidin-4-yl)-4.5-dimethylphenyl]propyl}amine [ No CAS ]
  • [ 255735-88-7 ]
  • N-{(1S)-1-[2-(1-[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}piperidin-4-yl)-4,5-dimethylphenyl]propyl}ethane-1,2-diamine trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
tert-Butyl (2-aminoethyl) carbamate (17.3 mg, 0.1 mmol), sodiumtriacetoxyborohydride (64 mg, 0.3 mmol) and glacial acetic acid (17 IL, 0. 3 MMOL) were added to a solution of 113 (50 mg, 0.1 mmol) in DCM (1.0 ML) and the resulting mixture allowed to stir at r. t. for 18 h. The reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (MGS04), filtered, and the filtrate concentrated IN VACUO. The crude residue was treated with TFA/DCM (1: 1,2. 0 ML) and after 30 min the volatiles were evaporated in vacuo. Purification of the crude residue by preparative reversed phase HPLC on YMC Pack Pro C18 (gradient elution; 0-71percent ACETONITRILE/WATER as eluent, 0. 1percent TFA modifier) gave 114 as the trifluoroacetate salt.
  • 9
  • [ 480450-83-7 ]
  • [ 255735-88-7 ]
  • [ 721927-29-3 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20 - 40℃; for 96h; After 10% palladium carbon (100 mg) was added to a methanol (30 ml) solution of the compound (1.00 g) obtained in Referential Example 339, the resulting mixture was stirred at room temperature for 14 hours under a hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (20 ml). The compound (1.12 g) obtained in Referential Example 9, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.15 g) and 1-hydroxybenzotriazole (0.676 g) were added. After stirring overnight at room temperature, stirring was conducted further at 40C for 4 days. The reaction mixture was concentrated under reduced pressure. Chloroform was added to the residue. The resulting mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue purified by chromatography (methylene chloride:methanol = 98:2 ? 95:5) on a silica gel column, whereby the title compound (1.01 g) was obtained.1H-NMR(CDCl3) delta: 1.20(3H,d,J=6.6Hz), 1.44(9H,s), 3.29-3.41(1H,m), 3.42-3.51(1H,m), 3.91(1H,br s), 4.55(1H,br s), 7.71(1H,dd,J=9.0,2.4Hz), 7.99(1H,br s), 8.20(1H,d,J=9.0Hz), 8.31(1H,d,J=2.4Hz), 9.73(1H,s). MS(ESI)m/z: 357(M+H)+.
  • 10
  • [ 149602-64-2 ]
  • [ 255735-88-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 14h; After 10percent palladium carbon (100 mg) was added to a methanol (30 ml) solution of the compound (1.00 g) obtained in Referential Example 339, the resulting mixture was stirred at room temperature for 14 hours under a hydrogen atmosphere. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (20 ml). The compound (1.12 g) obtained in Referential Example 9, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.15 g) and 1-hydroxybenzotriazole (0.676 g) were added. After stirring overnight at room temperature, stirring was conducted further at 40°C for 4 days. The reaction mixture was concentrated under reduced pressure. Chloroform was added to the residue. The resulting mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue purified by chromatography (methylene chloride:methanol = 98:2 --> 95:5) on a silica gel column, whereby the title compound (1.01 g) was obtained.1H-NMR(CDCl3) delta: 1.20(3H,d,J=6.6Hz), 1.44(9H,s), 3.29-3.41(1H,m), 3.42-3.51(1H,m), 3.91(1H,br s), 4.55(1H,br s), 7.71(1H,dd,J=9.0,2.4Hz), 7.99(1H,br s), 8.20(1H,d,J=9.0Hz), 8.31(1H,d,J=2.4Hz), 9.73(1H,s). MS(ESI)m/z: 357(M+H)+.
  • 11
  • [ 110-89-4 ]
  • [ 255735-88-7 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; methanol; (d) [(2R)-2-aminopropyl]carbamic acid, 1,1-dimethylethyl ester To a solution of the product from example 9, step (c) (3.8 g) in THF (100 ml) was added piperidine (5 ml) and the mixture allowed to stand for 1 hour at room temp. The mixture was evaporated to dryness and the residue purified (SiO2, 5percent methanol:dichloromethane as eluant) to give the subtitle compound as a colourless oil (1.7 g). NMR deltaH (CDCl3) 4.95 (1H, s), 3.13 (1H, m), 2.99 (1H, m), 2.87 (1H, m), 1.38 (9H, s), 1.08 (3H, d).
YieldReaction ConditionsOperation in experiment
Preparation 12 To a solution of dl-1,2-diaminopropane (1.48 g, 20.0 mmol) and sodium carbonate (2.73 g, 22.0 mmol) in dioxane (100.0 mL) and water (100.0 mL) was added di-tert-dicarbonate (4.80 g, 22.0 mmol) at room temperature. The resulted mixture was stirred for 14 hr. Dioxane was removed in vacuo. The precipitate was filtered off and the filtrate was concentrated in vacuo to dryness. The residue was triturated with EtOAc and then filtered. The filtrate was concentrated in vacuo to dryness to give a mixture of dl-1-amino-2-(1,1-dimethylethoxy)carbonylamino-propane and dl-2-amino-1-(1,1-dimethylethoxy)carbonylamino-propane which were not separable by normal chromatography method. The mixture was used for the reaction in Example 8.
  • 13
  • [ 104-88-1 ]
  • [ 255735-88-7 ]
  • C15H23ClN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% Example 1OA; tert-butyl {3-[(4-chlorobenzyl)amino]propyl}carbamate EPO <DP n="29"/>10 g (71.1 mmol) 4-chlorobenzaldehyde and 13.6 g (78.3 mmol) tert-butyl (2-aminopropyl)- carbamate are dissolved in 200 ml methanol and stirred for 2 h at room temperature. The solution is cooled to O0C and 13.5 g (355.7 mmol) sodium borohydride are carefully added. Water is added until a clear solution is formed and the mixture is stirred at room temperature overnight. The mixture is concentrated under vacuum, the residue is diluted with dichloromethane and the organic phase is washed with brine, dried over magnesium sulfate and concentrated under vacuum. The crude product is re-crystallized from petroleum ether to yield 8.9 g (42percent of th.) of the title compound as a solid.HPLC (method 6): R, = 4.03 min; MS (ESIpos): m/z = 299 (M+H)+1H-NMR (300 MHz, DMSOd6): delta = 7.35 (m, 4H), 6.70 (m, IH), 3.60 (s, 2H), 2.95 (m, 2H), 2.40 (m, 2H), 2.10 (bs, IH), 1.50 (m, 2H), 1.40 (s, 9H).
  • 14
  • [ 24424-99-5 ]
  • [ 78-90-0 ]
  • [ 255735-88-7 ]
  • 16
  • [ 69-72-7 ]
  • [ 255735-88-7 ]
  • [ 1204318-26-2 ]
YieldReaction ConditionsOperation in experiment
40% With 1H-imidazole; dicyclohexyl-carbodiimide; In ethyl acetate; at 0 - 20℃; To a solution of tert-butyl 2-aminopropylcarbamate (3.6 g, 20.6 mmol), 2-hydroxybenzoic acid (2.79 g, 20.6 mmol) and imidazole (1.41 g, 20.6 mmol) in EtOAc (100 mL) at 0° C. was slowly added a solution of DCC (4.26 g, 20.6 mmol) in EtOAc (50 mL). The reaction mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography, EtOAc/Petroleum ether (0-20percent) to afford tert-butyl 2-(2-hydroxybenzamido)propylcarbamate (2.4 g, 40percent) as a white solid.
  • 17
  • [ 6217-54-5 ]
  • [ 255735-88-7 ]
  • [ 1204318-28-4 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; HATU; In acetonitrile; at 0 - 20℃; Example 21; Preparation of N-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropyl)-2-hydroxybenzamide (14); To a solution of tert-butyl 2-aminopropylcarbamate (1.06 g, 6.09 mmol, prepared as previously described), DHA (2.0 g, 6.09 mmol) and Et3N (1.7 mL, 12.8 mmol) in CH3CN (40 mL) at 0° C. was added HATU (2.31 g, 6.09 mmol). The mixture was stirred (RT, 16 h) and concentrated under reduced pressure. The residue was diluted with brine (100 mL) and extracted with EA (2.x.100 mL). The combined organic layers were washed with saturated NaHCO3 (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with EA-PE (0-25percent) to afford tert-butyl 2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidopropylcarbamate (2.1 g, 70percent) as a light yellow oil. Mass calculated for C30H48N2O3=484.71; found: [M+H]+=485.6.
  • 18
  • 1-(N-tert-butoxycarbonylamino)-2-azidopropane [ No CAS ]
  • [ 255735-88-7 ]
YieldReaction ConditionsOperation in experiment
83.7% With hydrogen;palladium over charcoal; In methanol; at 20℃; under 760.051 Torr; for 16h; A mixture of afford tert-butyl 2-azidopropylcarbamate (7.0 g, 3.6 mmol) and Pd/C (0.7 g) in MeOH (250 mL) was stirred under a H2 (1 atm) atmosphere (RT, 16 h). The mixture was filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with saturated NH3 in MeOH-DCM (0-10percent) to afford tert-butyl 2-aminopropylcarbamate (5.1 g, 83.7percent) as a light yellow oil. 1HNMR (CDCl3): delta4.9 (bs, 1H, NH), 3.15 (m, 1H, CH), 3.0 (m, 1H, CH2), 2.8 (m, 1H, CH2), 1.7 (bs, 2H, NH2), 1.5 (s, 9H, CH3), 1.0 (d, 3H, CH3).
  • 19
  • [ 33252-28-7 ]
  • [ 255735-88-7 ]
  • [ 1059191-62-6 ]
YieldReaction ConditionsOperation in experiment
55% With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 90℃; for 12h;Inert atmosphere; Example 38A; tert-Butyl {2-[(5-cyanopyridin-2-yl)amino]propyl}carbamate 2-Chloro-5-cyanopyridine (477 mg, 3.4 mmol), tert-butyl (2-aminopropyl)carbamate (300 mg, 1.7 mmol) and potassium bicarbonate (345 mg, 3.4 mmol) are dissolved in DMF (10 ml) and stirred at 90° C. under argon for 12 h. The reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate (3.x.75 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. After removal of the solvent, the residue is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 10:1). 265 mg (55percent of theory) of the product are obtained as a solid.LCMS (method 4): Rt=3.21 min. (m/z=277 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.37 (d, 1H), 7.66 (d, 1H), 7.37 (d, 1H), 6.87 (br t, 1H), 6.50 (d, 1H), 4.05 (m, 1H), 3.02 (m, 2H), 1.37 (s, 9H), 1.07 (d, 3H).
  • 20
  • [ 1059191-32-0 ]
  • [ 255735-88-7 ]
  • [ 1059191-59-1 ]
YieldReaction ConditionsOperation in experiment
68% With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 120℃; for 12h;Inert atmosphere; Example 36A; tert-Butyl (2-[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}propyl)carbamate 5-Chloro-7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidine (Example 6A) (800 mg, 2.7 mmol), tert-butyl (2-aminopropyl)carbamate (700 mg, 4.0 mmol) and N,N-diisopropylethylamine (1.00 g, 8.0 mmol) are dissolved in DMSO (13 ml) and stirred at 120° C. under argon for 12 hours. The reaction mixture is diluted with water (100 ml) and extracted with ethyl acetate (3.x.75 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. Removal of the solvent results in a foam which is taken up in diethyl ether. The product precipitates as solid from the diethyl ether solution and is filtered off with suction and dried. 800 mg (68percent of theory) of the product are obtained as a solid.LCMS (method 3): Rt=2.04 min. (m/z=437 (M+H)+)1H-NMR (400 MHz, DMSO-d6): delta=8.04 (s, 1H), 7.75 (dd, 1H), 7.70 (d, 1H), 7.56 (d, 1H), 7.51 (m, 2H), 7.10 (s, 1H), 6.96 (t, 1H), 4.34 (m, 1H), 3.21 (m, 2H), 1.32 (s, 9H), 1.23 (d, 3H).
  • 21
  • [ 619-86-3 ]
  • [ 255735-88-7 ]
  • [ 1003577-91-0 ]
  • 22
  • [ 142818-01-7 ]
  • [ 255735-88-7 ]
  • [ 1003577-93-2 ]
  • 23
  • [ 6627-89-0 ]
  • [ 78-90-0 ]
  • [ 149632-73-5 ]
  • [ 255735-88-7 ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 16h;Reflux; (+/-)- ,2-diaminopropane (2.30 mL, 27.0 mmol) was dissolved in ethanol (100 mL) and 1 ,1-dimethy.ethyl phenyl carbonate (9.98 mL, 54.0 mmol) added. The mixture was heated to reflux for 16 hours, cooled to room temperature, and concentrated by rotovap. The residue was diluted with water before hydrochloric acid (1 M) was added carefully until the pH was ~3. The aqueous phase was washed 3 times withdichloromethane and then made strongly basic with sodium hydroxide (1 M). The aqueous phase and extracted 3 times with dichloromethane and the combined organic layers dried over sodium sulfate before being concentrated to give the title compound (2.98 g, 63percent) as a mixture (-85:15) of regioisomers. ES-LCMS m/z: 175 (M+1 ).
  • 24
  • [ 2094-74-8 ]
  • [ 255735-88-7 ]
  • C19H32N2O2 [ No CAS ]
  • 25
  • [ 18220-83-2 ]
  • [ 255735-88-7 ]
  • C20H34N2O2 [ No CAS ]
  • 26
  • [ 255735-88-7 ]
  • tert-butyl {2-[(1-adamantylmethyl)amino]propyl}carbamate [ No CAS ]
  • 27
  • [ 255735-88-7 ]
  • tert-butyl (2-[2-(1-adamantyl)ethyl]amino}propyl)carbamate [ No CAS ]
  • 28
  • 3-(3,3-diethyl-1-methoy-2-oxo-1-azaspiro[4.5]dec-7-en-8-yl)-1H-pyrrazole-4-carbaldehyde [ No CAS ]
  • [ 255735-88-7 ]
  • tert-butyl (-(((3-(3,3-diethyl-1-methoxy-2-oxo-1-azaspiro[4.5]decan-8-yl)-1-1H-pyrazol-4-yl)(methyl)amino)ethyl)(methyl)cabamate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.1% With sodium tris(acetoxy)borohydride; 1,2-dichloro-ethane; at 0 - 20℃; for 2h; To a stuffed solution of 3 -(3 ,3-diethyl- 1 -methoy-2-oxo- 1 -azaspiro [4.51 dec-7-en-8- yl)- 1 H-pyrrazole-4-carbaldehyde (0.58 g, 1.75 mmol) and tert-butyl(2- methylamino)ethyl)carbamate (0.495 g, 2.62mmol) in EDC (25 ml) was added sodium triacetoxy borohydride (1.11 g, 5.26 mmol) portionwise at 0 °C. The resulting mixture was stirred at rt for 2 h at which time the reaction mixture was diluted with water (30 ml) and extracted with ethyl acetate (2x20 ml) and the combined organic layers were dried over sodium sulphate. The solvent was removed under reduced pressure and the resulting crude was purified by column chromatography to give title compound (95.1percent) LCMS: mlz=504.4 [M+1].
  • 29
  • 3-(3,3-diethyl-1-methyl-2-oxo-1-azaspiro[4.5]dec-7-en-8-yl)-1H-(pyrazole-4)-carbaldehyde [ No CAS ]
  • [ 255735-88-7 ]
  • tert-butyl (2((3-(3,3-diethyl-1-methyl-2-oxo-1-azaspiro[4.5]dec-7-en-8-yl)-1H-pyrazol-4-yl)(methyl)(methyl)amino)ethyl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.9% With sodium tris(acetoxy)borohydride; In ethylene dibromide; at 20 - 60℃; for 1h; To a stuffed solution of 3-(3,3-diethyl- 1 -methyl-2-oxo- 1 -azaspiro[4.5]dec-7-en-8- yl)-1H-pyrazole4)carbaldehyde(0. 1 g, 0.332 mmol) and tertbutyl(2methylamino)ethyl)carbamate (0.093 g, 0.497 mmol) in EDC (4 ml) at rt, were added sodium triacetoxy borohydride (0.210 g,0.995 mmol) in portion wise, stirred reaction 1 h at 60 °C. The reaction was diluted by water and extracted with DCM (2x15 ml), washed with sodium bicarbonate solution, the combined organic layers were dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure and the resulting crude was purified by column chromatography using mobile phase 5percent methanol in dichloromethane to give title compound (64.9percent). LCMS: mlz=487.35 [M+1].
  • 30
  • 3-(4-((2,2,2-trifluoroethoxy)methyl)cyclohex-1-en-1-yl)-1H-pyrazole-4-carbaldehyde [ No CAS ]
  • [ 255735-88-7 ]
  • tert-butyl methyl(2-(methyl((1-(tetrahydro-2H-pyran-2-yl)-3-(4-((2,2,2-trifluoroethoxy)methyl)cyclohex-1-en-1-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.46% With sodium tris(acetoxy)borohydride; In ethylene dibromide; at 50 - 55℃; for 2h; To a 3-neck 10 ml RBF, 3- (4- ((2,2,2-trifluoroethoxy)methyl)cyclohex- 1-en-i -yl)1H-pyrazole-4-carbaldehyde (0.160 g, 0.55 mmol) and tert-butyl methyl(2-(methylamino)ethyl)carbamate (0.157 g, 0.83 mmol) was dissolved in ethylene dichloride (4 ml) at 5 °C temperature. Sodium triacetoxy borohydride (0.353 g, 1.66 mmol) was added portionwise. After addition, the ice bath was removed and reaction mixture was stirred at 50- 55 °C for 2 h. Sodium bicarbonate (sat. aq.) was added to reaction mixture and extracted by DCM (3x20 ml), dried over Na2504. The organic layers were concentrated and the crude product was purified by silica gel column chromatography using mobile phase 0-16percent ethyl acetate in hexane to get the title compound as a pale yellow liquid. (85.46percent). LCMS:mlz=46 1.66 [M+1].
  • 31
  • 3-[3,3-dimethyl-1-oxaspiro[4.5]dec-7-en-8-yl]-1H-pyrazole-4-carbaldehyde [ No CAS ]
  • [ 255735-88-7 ]
  • tert-butyl (2-(((3-(3,3-dimethyl-1-oxaspiro[4.5]dec-7-en-8-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
29.9% With sodium tris(acetoxy)borohydride; In ethylene dibromide; at 0 - 55℃; for 2h; To a 3-necked 25m1 RBF, 3-(3,3-dimethyl- 1 -oxaspiro[4.5]dec-7-en-8-yl)- 1H- pyrazole-4-carbaldehyde (0.240 g, 0.92 mmol) and tert-butyl (2- aminoethyl)(methyl)carbamate (0.241 g, 1.38 mmol) was dissolved in EDC (6 ml) at 0 °C. Sodium triacetoxy borohydride (0.586 g, 2.76 mmol) was added portionwise. After addition, the ice bath was removed and the reaction mixture was stuffed at 55 °C for 2 h. The reaction mixture was neutralized by sodium bicarbonate (sat. 20 ml) and extracted by DCM (3x25 ml), dried over Na2504. The solvent was evaporated to obtain crude product which was purified using silica column chromatography using mobile phase 0-2percent MeOH in DCM to afford the title compound as a thick pale yellow oil (29.9percent). LCMS: mlz=419.5 [M+1].
  • 32
  • 3-(1,5-diethyl-8-oxabicyclo[3.2.1]oct-2-en-3-yl)-1H-pyrazole-4-carbaldehyde [ No CAS ]
  • [ 255735-88-7 ]
  • tert-butyl (2-(((3-(1,5-diethyl-8-oxabicyclo[3.2.1]oct-2-en-3-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92.9% To a stuffed solution of 3-( 1 ,5-diethyl-8-oxabicyclo[3 .2.11 oct-2-en-3-yl)- 1H- pyrazole-4-carbaldehyde (0.94 g, 3.61 mmol) in ethylene dichloride (10 ml) was added with tert-butyl (2-(dimethylamino)ethyl) (methyl)carbamate (1.01 g, 5.42 mmol) and stuffed it for 30 mm at room temperature. This was added with sodium triacetoxy borohydride (2.29 g,10.8 mmol) portionwise and stirred it for 1 h. Reaction mixture was basified with sodium bicarbonate until basic and extracted with DCM (3x50 ml). The combined organic layer was dried over anhydrous sodium sulphate and concentrated to obtain yellow sticky liquid product (92.9percent). LCMS: mlz=433.7 [M+1].
  • 33
  • [ 2937-50-0 ]
  • [ 255735-88-7 ]
  • C12H22N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.2 g In dichloromethane; at 0 - 25℃; for 1h; 10385] Step 1: To a solution of allyl carbonochloridate (1.66 g, 13.77 mmol, 1.46 mL, 3.00 equiv.) in DCM (10.00 mL) was added compound 1 (800.00 mg, 4.59 mmol, 1.00 equiv.) slowly at 0° C. The mixture was stirred at 25° C. for 1 hout The mixture was quenched by addition 10percent citric acid solution, and extracted with DCM (45 mE). The combined organic layers were dried over Na2SO4, and filtered. Concentration under reduced pressure resulted in 1 .2 g of compound 2.
  • 34
  • [ 394-47-8 ]
  • [ 255735-88-7 ]
  • (+/-)-tert-butyl (2-((2-cyanophenyl)amino)propyl)carbamate [ No CAS ]
  • 35
  • [ 394-47-8 ]
  • [ 255735-88-7 ]
  • (+/-)-tert-butyl (2-((2-acetylphenyl)amino)propyl)carbamate [ No CAS ]
 

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