2-Bromo-5-((tert-butoxycarbonyl)amino)thiazole-4-carboxylic acid → HCID 86679974, compound

HRID 1915761Notes

Reaction equation

HRID 1915761 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH2:22][CH:23]([F:25])[F:24])[C:6]=1[N:7]1[CH2:13][CH2:12][CH2:11][C@H:10]([N:14]([CH3:21])[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:9][CH2:8]1.[Br:26][C:27]1[S:28][C:29]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[C:30]([C:32](O)=[O:33])[N:31]=1>>[Br:26][C:27]1[S:28][C:29]([NH:35][C:36](=[O:37])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])=[C:30]([C:32](=[O:33])[NH:1][C:2]2[CH:3]=[N:4][N:5]([CH2:22][CH:23]([F:25])[F:24])[C:6]=2[N:7]2[CH2:13][CH2:12][CH2:11][C@H:10]([N:14]([CH3:21])[C:15](=[O:20])[C:16]([F:18])([F:17])[F:19])[CH2:9][CH2:8]2)[N:31]=1

Participants

3

Reactant 2

HCID 581821562-Bromo-5-((tert-butoxycarbonyl)amino)thiazole-4-carboxylic acidHCID 86679975HCID 86679975, compound

Product 1

HCID 86679974HCID 86679974, compound

Procedure

Following the procedure for Intermediate 7 starting from (S)—N-(1-(4-amino-1-(2,2-difluoroethyl)-1H-pyrazol-5-yl)azepan-4-yl)-2,2,2-trifluoro-N-methylacetamide and 2-bromo-5-(tert-butoxycarbonylamino)-thiazole-4-carboxylic acid afforded (S)-tert-butyl 2-bromo-4-(1-(2,2-difluoroethyl)-5-(4-(2,2,2-trifluoro-N-methylacetamido)azepan-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate as a pale pink gum (80 mg 57%). 1H NMR (400 MHz, CDCl3) δ 10.27 (s, 1H), 8.31 and 8.27 (2s, 1H), 7.88 and 7.85 (2s, 1H), 6.34-6.05 (m, 1H), 4.41-4.31 (m, 2H), 3.42-3.29 (m, 5H), 3.10 and 2.95 (2s, 3H), 2.08-1.75 (m, 4H), 1.40-1.15 (m, 2H).

Sources & evidence

ORD record
ord-560d8483976942afb977bf6632d17293
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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