5-((Tert-butoxycarbonyl)amino)-2-(pyridin-2-yl)thiazole-4-carboxylic acid → 5-amino-N-[5-(4-amino-5-methoxy-azepan-1-yl)-1-methyl-pyrazol-4-yl]-2-(2-pyridyl)thiazole-4-carboxamide

HRID 1915910Notes

Reaction equation

HRID 1915910 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:24])[C:6]=1[N:7]1[CH2:13][CH2:12][C@@H:11]([O:14][CH3:15])[C@H:10]([NH:16]C(=O)OC(C)(C)C)[CH2:9][CH2:8]1.C(OC([NH:32][C:33]1[S:37][C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)=[N:35][C:34]=1[C:44](O)=[O:45])=O)(C)(C)C>>[NH2:32][C:33]1[S:37][C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)=[N:35][C:34]=1[C:44]([NH:1][C:2]1[CH:3]=[N:4][N:5]([CH3:24])[C:6]=1[N:7]1[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH:10]([NH2:16])[CH2:9][CH2:8]1)=[O:45]

Participants

3

Reactant 2

HCID 581821985-((Tert-butoxycarbonyl)amino)-2-(pyridin-2-yl)thiazole-4-carboxylic acidHCID 86680114tert-butyl ((4R,5R)-1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-methoxyazepan-4-yl)carbamate

Product 1

HCID 749831915-amino-N-[5-(4-amino-5-methoxy-azepan-1-yl)-1-methyl-pyrazol-4-yl]-2-(2-pyridyl)thiazole-4-carboxamide

Procedure

Following the procedure Example 101, reacting tert-butyl ((4R,5R)-1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-methoxyazepan-4-yl)carbamate and 5-((tert-butoxycarbonyl)amino)-2-(pyridin-2-yl)thiazole-4-carboxylic acid gave racemic 322 (58.4 mg, 41% over two steps). 1H NMR (400 MHz, DMSO) δ 8.89 (s, 1H), 8.54 (d, J=4.7 Hz, 1H), 8.17 (d, J=8.0 Hz, 1H), 7.89 (t, J=7.7 Hz, 1H), 7.62-7.47 (m, 3H), 7.43-7.31 (m, 1H), 3.64 (s, 3H), 3.27 (s, 3H), 3.23-2.91 (m, 6H), 2.15-2.00 (m, 1H), 1.92-1.80 (m, 1H), 1.79-1.55 (m, 2H). LCMS (ES+) m/z 443 (M+1)

Workup

  1. customgave racemic 322 (58.4 mg, 41% over two steps)

Sources & evidence

ORD record
ord-e9b796ba3ccb420ca94488997f5c09cf
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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