HOAt → N-(4-Bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-(trifluoromethyl)quinolin-7-yl)acetamide

HRID 2098064Notes

Reaction equation

HRID 2098064 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([CH2:13][C:14]([OH:16])=O)=[CH:8][CH:9]=2)[N:4]=1.[Br:19][C:20]1[C:21]([C:26]2[NH:30][CH:29]=[N:28][N:27]=2)=[C:22]([NH2:25])[S:23][CH:24]=1.C1C=NC2N(O)N=NC=2C=1>>[Br:19][C:20]1[C:21]([C:26]2[NH:30][CH:29]=[N:28][N:27]=2)=[C:22]([NH:25][C:14](=[O:16])[CH2:13][C:7]2[CH:6]=[C:5]3[C:10]([CH:11]=[CH:12][C:3]([C:2]([F:1])([F:18])[F:17])=[N:4]3)=[CH:9][CH:8]=2)[S:23][CH:24]=1

Participants

4

Reactant 3

HCID 181649HOAtHCID 687547832-(2-(Trifluoromethyl)quinolin-7-yl)acetic acidHCID 178509325HCID 178509325, compound

Product 1

HCID 178520190N-(4-Bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-(trifluoromethyl)quinolin-7-yl)acetamide

Procedure

The title compound was synthesized via protocol B from 2-(2-(trifluoromethyl)quinolin-7-yl)acetic acid and 4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine, using HOAt instead of HOBt. HPLC purification afforded the product as a white solid. HPLC method [7], retention time 8.68 min; MS (ESI) 484.2 (MH+, 81Br); 1H NMR (300 MHz, CD3OD) δ 8.76 (d, J=9.5 Hz, 1H), 8.25 (d, J=9.0 Hz, 1H), 7.96 (dd, J=8.7, 7.3 Hz, 1H), 7.92-7.81 (m, 1H), 7.11-6.97 (m, 1H), 4.45 (s, 2H).

Workup

  1. customHPLC purification

Sources & evidence

ORD record
ord-e873cd46d85a4415acd73bbf6b2f525f
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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