5-((Tert-butoxycarbonyl)amino)-2-(pyridin-2-yl)thiazole-4-carboxylic acid → 5-amino-N-(5-((4S,5S)-4-amino-5-fluoroazepan-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-(pyridin-2-yl)thiazole-4-carboxamide

HRID 1915909Notes

Reaction equation

HRID 1915909 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:22])[C:6]=1[N:7]1[CH2:13][CH2:12][CH:11]([F:14])[CH:10]([NH:15]C(=O)C(F)(F)F)[CH2:9][CH2:8]1.C(OC([NH:30][C:31]1[S:35][C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[N:33][C:32]=1[C:42](O)=[O:43])=O)(C)(C)C>>[NH2:30][C:31]1[S:35][C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[N:33][C:32]=1[C:42]([NH:1][C:2]1[CH:3]=[N:4][N:5]([CH3:22])[C:6]=1[N:7]1[CH2:13][CH2:12][C@H:11]([F:14])[C@@H:10]([NH2:15])[CH2:9][CH2:8]1)=[O:43]

Participants

3

Reactant 2

HCID 581821985-((Tert-butoxycarbonyl)amino)-2-(pyridin-2-yl)thiazole-4-carboxylic acidHCID 86680076N-(1-(4-Amino-1-methyl-1H-pyrazol-5-yl)-5-fluoroazepan-4-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 749831655-amino-N-(5-((4S,5S)-4-amino-5-fluoroazepan-1-yl)-1-methyl-1H-pyrazol-4-yl)-2-(pyridin-2-yl)thiazole-4-carboxamideYield 74%

Procedure

Following the procedure for Example 107 starting from N-(1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-fluoroazepan-4-yl)-2,2,2-trifluoroacetamide and 5-(tert-butoxycarbonylamino)-2-(pyridin-2-yl)thiazole-4-carboxylic acid gave 298 as a pale yellow solid (418 mg, 74% over 2 steps). 1H NMR (400 MHz, CDCl3) δ 8.54 (d, J=4.9 Hz, 1H), 8.40 (s, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.78-7.73 (m, 2H), 7.28-7.23 (m, 1H), 6.26 (s, 2H), 4.51 (dtd, J=48.0, 8.8, 3.8 Hz, 1H), 3.73 (s, 3H), 3.37-3.20 (m, 5H), 2.35-2.21 (m, 1H), 2.18-2.04 (m, 1H), 2.02-1.92 (m, 1H), 1.79-1.66 (m, 1H). Alkyl NH2 not seen. LCMS (ES+) m/z 431 (M+1)

Sources & evidence

ORD record
ord-2bcfa3082f2b4830817809195cf57def
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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