Diisopropylethylamine → HCID 58388245, compound

HRID 2047354Notes

Reaction equation

HRID 2047354 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([OH:13])=O)=[O:7])([CH3:4])[CH3:3].[Cl:20][C:21]1[C:25]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)=[C:24]([Cl:32])[S:23][C:22]=1[NH2:33].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>ClCCl>[Cl:20][C:21]1[C:25]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)=[C:24]([Cl:32])[S:23][C:22]=1[NH:33][C:11](=[O:13])[CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 2733179PyBroP2×HCID 27559923-[(tert-Butoxycarbonyl)amino]-2-phenylpropanoic acid2×HCID 58388241HCID 58388241, compound

Product 1

HCID 58388245HCID 58388245, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-phenylpropanoic acid (342 mg, 1.290 mmol), [3,5-dichloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]amine (320 mg, 1.290 mmol) and DIPEA (1.126 ml, 6.45 mmol) in dichloromethane (12.100 ml) at 25° C. was added bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (723 mg, 1.548 mmol) in one portion. After 12 h, additional DIPEA (1.126 ml, 6.45 mmol), 3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-phenylpropanoic acid (342 mg, 1.290 mmol) and Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (723 mg, 1.548 mmol) were added and the solution stirred 24 h. The reaction mixture was then dry loaded onto silica and purified by chromatography (0-70% EtOAc in hexanes) affording 1,1-dimethylethyl (3-{[3,5-dichloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]amino}-3-oxo-2-phenylpropyl)carbamate (320 mg, 0.491 mmol, 38.1% yield) as an yellow oil: LCMS (ES) m/e 495, 497 (M, M+2)+.

Workup

  1. customThe reaction mixture was then dry
  2. custompurified by chromatography (0-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c417f103704d434089fad376f970bb97
Source dataset
uspto-grants-2013_11
Patent number
US08592475B2

Reaction notes

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