4-Fluoro-3-(trifluoromethyl)aniline → HCID 24960672, compound

HRID 2196594Notes

Reaction equation

HRID 2196594 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:25][CH2:24][C:23]2[C:22]([C:26](Cl)=[O:27])=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]1=[O:29].[F:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][C:32]=1[C:38]([F:41])([F:40])[F:39].C(N(CC)C(C)C)(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][N:16]1[CH2:25][CH2:24][C:23]2[C:22]([C:26]([NH:35][C:34]3[CH:36]=[CH:37][C:31]([F:30])=[C:32]([C:38]([F:41])([F:39])[F:40])[CH:33]=3)=[O:27])=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]1=[O:29]

Participants

5

Reactant 3

HCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 59756881HCID 59756881, compound

Product 1

HCID 24960672HCID 24960672, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-((6,7-dimethoxyquinolin-4-yl)methyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carbonyl chloride (75 mg, 0.168 mmol) was suspended in dichloromethane (1 mL) then added a solution of 4-fluoro-3-trifluoromethylaniline (36 mg, 0.201 mmol) in dichloromethane (0.5 mL) and N,N-diisopropylethylamine (65 mg, 0.504 mmol). The reaction mixture was stirred at room temperature for 2 days. The reaction mixture was purified directly by silica gel chromatography (3% methanol/dichloromethane) to afford 2-((6,7-dimethoxyquinolin-4-yl)methyl)-N-(4-fluoro-3-(trifluoromethyl)phenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-5-carboxamide (46 mg) as a pale yellow solid. MS (ESI, pos. ion) m/z: 554.2 (M+1).

Workup

  1. customThe reaction mixture was purified directly by silica gel chromatography (3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-eae1106046e445ce9b7bfb178f42a224
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

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