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

HRID 1915913Notes

Reaction equation

HRID 1915913 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]=[C:42]([CH3:44])[CH:41]=[CH:40][C:39]=2[F:45])=[N:35][C:34]=1[C:46](O)=[O:47])=O)(C)(C)C>>[NH2:32][C:33]1[S:37][C:36]([C:38]2[CH:43]=[C:42]([CH3:44])[CH:41]=[CH:40][C:39]=2[F:45])=[N:35][C:34]=1[C:46]([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:47]

Participants

3

Reactant 2

HCID 866801125-((Tert-butoxycarbonyl)amino)-2-(2-fluoro-5-methylphenyl)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 749831945-amino-N-[5-(4-amino-5-methoxy-azepan-1-yl)-1-methyl-pyrazol-4-yl]-2-(2-fluoro-5-methyl-phenyl)thiazole-4-carboxamideYield 40%

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-(2-fluoro-5-methylphenyl)thiazole-4-carboxylic acid gave 325 (70.8 mg, 40% over two steps). 1H NMR (400 MHz, DMSO) δ 8.98 (s, 1H), 8.07 (d, J=7.4 Hz, 1H), 7.48 (s, 1H), 7.40 (s, 2H), 7.23 (d, J=9.0 Hz, 2H), 3.64 (s, 3H), 3.24 (s, 4H), 3.23-2.86 (m, 8H), 2.37 (s, 3H), 2.11-1.95 (m, 1H), 1.91-1.79 (m, 1H), 1.79-1.53 (m, 2H). LCMS (ES+) m/z 474 (M+1).

Sources & evidence

ORD record
ord-cdee3f97a08642adb611094a2ff69e1f
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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