Cyclopropylamine → (S)-2-[4-(5-Cyclopropylcarbamoyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

HRID 737191Notes

Reaction equation

HRID 737191 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:31])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[O:24][C:25]([C:28](O)=[O:29])=[CH:26][CH:27]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:43]=[CH:44][CH:45]=[N:46]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1(N)CC1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:31])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[O:24][C:25]([C:28](=[O:29])[NH:46][CH:45]3[CH2:43][CH2:44]3)=[CH:26][CH:27]=2)[N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

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 86616437(S)-2-[4-(5-Carboxy-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 57849692(S)-2-[4-(5-Cyclopropylcarbamoyl-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester

Procedure

In a similar procedure as described for the synthesis of Compound 5352 (Example 352), treatment of (S)-2-[4-(5-Carboxy-furan-2-yl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester with HATU (0.23 g, 0.6 mmol), DIEA (0.2 mL, 1.53 mmol), and cyclopropylamine (0.1 1 mL) furnished the desired product. 1HNMR (DMSO-d6) δ(ppm) 12.59-12.57 (d, 1H), 8.42-8.39 (m, 1H), 7.64-7.62 (d, 1H), 7.36-7.30 (m, 2H), 7.14-7.10 (m, 3H), 6.73-6.70 (m, 1H), 5.10-4.87 (m, 2H), 4.51-4.43 (m, 2H), 3.52-3.36 (m, 2H), 2.80-2.77, (m, 2H), 2.27-2.24 (m, 1H), 1.94-1.83 (m, 3H), 0.73-0.58 (m, 4H); MS: 481.2 (M+H+).

Sources & evidence

ORD record
ord-0e6025725e3f4c88ba59a3a706b0fb21
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

Loading…