HCID 68754558, compound → HCID 178520285, compound

HRID 2098062Notes

Reaction equation

HRID 2098062 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:12]=[C:11]([CH2:13][C:14]([OH:16])=O)[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[F:19][C:20]([F:36])([F:35])[C:21]1[CH:30]=[C:29]2[C:24]([CH:25]=[CH:26][CH:27]=[N:28]2)=[C:23]([CH2:31][C:32]([OH:34])=O)[CH:22]=1.[Br:37][C:38]1[C:39]([C:44]2[NH:48][CH:47]=[N:46][N:45]=2)=[C:40]([NH2:43])[S:41][CH:42]=1>>[Br:37][C:38]1[C:39]([C:44]2[NH:48][CH:47]=[N:46][N:45]=2)=[C:40]([NH:43][C:14](=[O:16])[CH2:13][C:11]2[CH:10]=[C:9]3[C:4]([CH:5]=[CH:6][CH:7]=[N:8]3)=[C:3]([C:2]([F:1])([F:18])[F:17])[CH:12]=2)[S:41][CH:42]=1.[Br:37][C:38]1[C:39]([C:44]2[NH:48][CH:47]=[N:46][N:45]=2)=[C:40]([NH:43][C:32](=[O:34])[CH2:31][C:23]2[CH:22]=[C:21]([C:20]([F:19])([F:36])[F:35])[CH:30]=[C:29]3[C:24]=2[CH:25]=[CH:26][CH:27]=[N:28]3)[S:41][CH:42]=1

Participants

5

Reactant 3

HCID 68754558HCID 68754558, compoundHCID 68758750HCID 68758750, compoundHCID 178509325HCID 178509325, compound

Product 2

HCID 178520285HCID 178520285, compoundHCID 178520286HCID 178520286, compound

Procedure

2-(5-(trifluoromethyl)quinolin-7-yl)acetic acid and the mixture of 2-(7-(trifluoromethyl)quinolin-5-yl)acetic acid (28.3 mg, 0.11 mmol) and 4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine (23 mg, 0.094 mmol) were treated according to protocol A. The crude product mixture was purified by HPLC to afford N-(4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(5-(trifluoromethyl)quinolin-7-yl)acetamide and N-(4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(7-(trifluoromethyl)quinolin-5-yl)acetamide. LCMS method [13], retention time (min) 10.100 and 10.386; MS (ESI) 482.0 (MH+, 79Br); 1H NMR (300 MHz, CD3OD) δ 9.01 (dd, J=4.3, 1.6 Hz, 1H), 8.62 (d, J=8.4 Hz, 1H), 8.41 (s, 1H), 7.98 (s, 1H), 7.70 (dd, J=8.7, 4.3 Hz, 1H), 4.50 (s, 2H).

Workup

  1. additionwere treated
  2. customThe crude product mixture was purified by HPLC

Sources & evidence

ORD record
ord-4f4c9b5382984c119e8e735ddbea11a8
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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