Cyclopropylamine → HCID 57849761, compound

HRID 737198Notes

Reaction equation

HRID 737198 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]([NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][N:25]=2)[N:23]=1)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:44]=[CH:45][CH:46]=[N:47]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>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:17])[NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24]2[CH:32]=[CH:31][C:27]([C:28](=[O:29])[NH:47][CH:46]3[CH2:44][CH2:45]3)=[CH:26][N:25]=2)[N:23]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

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 86616444HCID 86616444, compound

Product 1

HCID 57849761HCID 57849761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-{2-[((S)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-thiazol-4-yl}-nicotinic acid (0.18 g, crude), HATU (0.07 g, 0.18 mmol)), and DIEA (0.1 mL, 0.77 mmol) in DMF (5 mL) was stirred at room temperature for 30 min. then cyclopropylamine (0.030 ml, 0.4 mmol) was added and the reaction mixture was stirred at room temperature overnight. Purification by reverse phase HPLC furnished the desired product. 1HNMR (DMSO-d6) δ(ppm) 12.58-12.57 (d, 1H), 9.03 (s, 1H), 8.72-8.71 (d, 1H), 8.34-8.31 (m, 1H), 8.07-8.00 (m,2H), 7.44-7.38 (m, 2H), 7.22-7.12 (m, 2H), 5.17-4.95 (m, 2H), 4.61-4.55 (m, 1H), 3.59-3.52, (m, 2H), 2.95-2.90 (m,1H), 2.34-2.32 (m, 1H), 2.04-1.92 (m, 3H), 0.80-0.78 (m,4H); MS: 492.1 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customPurification by reverse phase

Sources & evidence

ORD record
ord-18fa1afcc4c446dca44caa8cc363c5a2
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

Loading…