4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine → N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(8-fluoroisoquinolin-5-yl)acetamide

HRID 2098089Notes

Reaction equation

HRID 2098089 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][C:13]([OH:15])=O)=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.[Br:16][C:17]1[C:18]([C:23]2[NH:27][N:26]=[CH:25][N:24]=2)=[C:19]([NH2:22])[S:20][CH:21]=1>>[Br:16][C:17]1[C:18]([C:23]2[NH:27][N:26]=[CH:25][N:24]=2)=[C:19]([NH:22][C:13](=[O:15])[CH2:12][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[C:11]3[C:6]=2[CH:7]=[CH:8][N:9]=[CH:10]3)[S:20][CH:21]=1

Participants

3

Reactant 2

HCID 596366864-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amineHCID 687588832-(8-Fluoroisoquinolin-5-yl)acetic acid

Product 1

HCID 56682209N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(8-fluoroisoquinolin-5-yl)acetamide

Procedure

The title compound was prepared from 2-(8-fluoroisoquinolin-5-yl)acetic acid and 4-bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-amine using protocol B. Retention time (min)=1.987, method [7], MS (ESI) 432.0 (M+H); 1H NMR (300 MHz, CD3OD) δ 9.74 (s, 1H), 8.66 (d, J=6.6 Hz, 1H), 8.30 (d, J=6.1 Hz, 1H), 8.20 (b s, 1H), 8.1 (dd, J=8.24, 5.5 Hz, 1H), 7.67 (dd, J=9.9, 7.7 Hz, 1H), 7.1 (s, 1H), 4.46 (s, 2H).

Sources & evidence

ORD record
ord-a426842e100d4b5786de342dd3650c0f
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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