4-Chloro-6-fluoro-2-(trifluoromethyl)quinoline → HCID 178523789, compound

HRID 2415617Notes

Reaction equation

HRID 2415617 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)[CH2:4][CH2:3]1.Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:30])[CH:28]=2)[N:23]=[C:22]([C:31]([F:34])([F:33])[F:32])[CH:21]=1>CN1C(=O)CCC1>[F:16][C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([F:17])[CH:13]=1)[C:9]([NH:8][C@H:5]1[CH2:4][CH2:3][C@@H:2]([NH:1][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([F:30])[CH:28]=3)[N:23]=[C:22]([C:31]([F:32])([F:33])[F:34])[CH:21]=2)[CH2:7][CH2:6]1)=[O:18]

Participants

4

Reactant 2

HCID 27365914-Chloro-6-fluoro-2-(trifluoromethyl)quinolineHCID 22641525N-(4-Aminocyclohexyl)-3,5-difluorobenzamide

Product 1

HCID 178523789HCID 178523789, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of N-(4-Amino-cyclohexyl)-3,5-difluorobenzamide (30 mg, 0.12 mmol) in NMP (1.0 mL) was treated with 4-chloro-6-fluoro-2-trifluoromethyl-quinoline (1 eq) and 3 eq (0.045 mL) TEA. The reaction was heated to 220 C in the microwave for 15 minutes. The crude compound was purified by reverse phase HPLC to provide the desired compound. MS (ESI (+)) m/e 468 (M+H)+; 1H NMR (500 MHz, DMSO) δ ppm 8.32 (m, 2 H), 7.98 (m, 1 H), 7.67 (m, 1 H), 7.58 (m, 2 H), 7.44 (m, 1 H), 7.15 (d, 1 H), 6.82 (s, 1 H), 1.95 (m, 4 H), 1.65-1.88 (m, 4 H).

Workup

  1. temperatureThe reaction was heated to 220 C in the microwave for 15 minutes
  2. customThe crude compound was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4787ccb1b4b842df84cd8b6cab01970f
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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