Cyclopropylamine → (S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tertbutyl ester

HRID 737207Notes

Reaction equation

HRID 737207 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:29])[NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([OH:28])=O)=[CH:22][CH:21]=2)[N:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2[CH:41]=[CH:42][CH:43]=[N:44]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1(N)CC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:29])[NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[NH:44][CH:43]3[CH2:41][CH2:42]3)=[CH:22][CH:21]=2)[N:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86616447(S)-2-[4-(4-carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59140902(S)-2-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tertbutyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-2-[4-(4-carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.51 g, 1.22 mmol), HATU (0.47 g, 1.24 mmol)), and DIEA (0.2 mL, mmol) in DMF (10.0 mL) was stirred at room temperature for 1 h. Cyclopropyl amine (0.2 mL, 1.53 mmol) was added and the reaction mixture was stirred at room temperature overnight. The resulting mixture was purified by reverse phase HPLC to furnish the desired product. 1HNMR (DMSO-d6) δ(ppm) 12.45-12.40 (m, 1H), 8.44-8.43 (d, 1H), 7.95-7.2 (m, 5H), 4.43-4.34 (m, 1H), 2.97-2.82 (m, 2H), 2.26-2.19 (m, 1H), 1.94-1.79 (m, 3H), 1.39-1.24 (m, 9H), 0.73-0.55 (m, 4H); MS: 457.2 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe resulting mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f3c2df585cc14bb08eb5b281f3a0f2b9
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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