4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine → 2-(benzo[d]thiazol-7-yl)-N-(4-bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)acetamide

HRID 2098071Notes

Reaction equation

HRID 2098071 reaction equation
[S:1]1[C:5]2[C:6]([CH2:10][C:11]([OH:13])=O)=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Br:14][C:15]1[C:16]([C:21]2[NH:25][N:24]=[CH:23][N:22]=2)=[C:17]([NH2:20])[S:18][CH:19]=1>>[S:1]1[C:5]2[C:6]([CH2:10][C:11]([NH:20][C:17]3[S:18][CH:19]=[C:15]([Br:14])[C:16]=3[C:21]3[NH:25][N:24]=[CH:23][N:22]=3)=[O:13])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 596366864-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amineHCID 687568187-Benzothiazoleacetic acid

Product 1

HCID 687848842-(benzo[d]thiazol-7-yl)-N-(4-bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)acetamide

Procedure

The title compound was prepared from 2-(benzo[d]thiazol-7-yl)acetic acid (25.5 mg, 0.13 mmol) and 4-bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-amine (22.3 mg, 0.093 mmol) according to protocol A. The crude product was purified by prep HPLC. LCMS Retention time (min)=4.075, method [7], MS (ESI) 421.9 (M+H). 1H NMR (CDCl3) δ 12.39 (s, 1H), 9.02 (s, 1H), 8.22, (d, J=6.6 Hz, 1H), 7.65-7.61 (m, 1H), 7.54 (s, 1H), 7.55-7.49 (m, 1H), 6.90 (s, 1H), 4.19 (s, 2H).

Workup

  1. customThe crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-cac66eaecef7459bad41b794a9d2d5b3
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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