2-(Isoquinolin-8-YL)acetic acid → N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(isoquinolin-8-yl)acetamide

HRID 2098014Notes

Reaction equation

HRID 2098014 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([OH:14])=O)[CH:4]=[CH:3][N:2]=1.[Br:15][C:16]1[C:17]([C:22]2[NH:26][N:25]=[CH:24][N:23]=2)=[C:18]([NH2:21])[S:19][CH:20]=1>>[Br:15][C:16]1[C:17]([C:22]2[NH:26][N:25]=[CH:24][N:23]=2)=[C:18]([NH:21][C:12](=[O:14])[CH2:11][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[CH:1]=[N:2][CH:3]=[CH:4]3)[S:19][CH:20]=1

Participants

3

Reactant 2

HCID 179072422-(Isoquinolin-8-YL)acetic acidHCID 596366864-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine

Product 1

HCID 68786765N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(isoquinolin-8-yl)acetamide

Procedure

N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(isoquinolin-8-yl)acetamide was prepared from 2-(isoquinolin-8-yl)acetic acid (53 mg, 0.286 mmol) and 4-bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-amine (35 mg, 0.143 mmol) according to protocol A. Retention time (min)=1.769, method [7], MS (ESI) 414.0 (M+H); 1H NMR (300 MHz, CD3OD) δ 9.84 (bs, 1H), 8.55 (bs, 1H), 8.41 (d, J=6.0 Hz, 1H), 8.26-8.23 (m, 2H), 8.18 (dd, J=8.1, 7.2 Hz, 1H), 7.99 (d, J=4.0 Hz, 1H), 7.09 (s, 1H), 4.61 (s, 2H).

Sources & evidence

ORD record
ord-a3d48eecb9a943439a5c95eea19839e9
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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