3-(Trifluoromethyl)aniline → HCID 178428514, compound

HRID 1898403Notes

Reaction equation

HRID 1898403 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[NH:13][C:12]3[C:14]4[CH2:15][C:16]([CH3:26])([CH3:25])[O:17][C:18]=4[C:19]([C:21]([O:23]C)=O)=[CH:20][C:11]=3[N:10]=2)=[C:6]([CH3:27])[CH:5]=[CH:4][N:3]=1.[F:28][C:29]([F:38])([F:37])[C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([NH:8][C:9]2[NH:13][C:12]3[C:14]4[CH2:15][C:16]([CH3:25])([CH3:26])[O:17][C:18]=4[C:19]([C:21]([NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[C:30]([C:29]([F:28])([F:37])[F:38])[CH:31]=4)=[O:23])=[CH:20][C:11]=3[N:10]=2)=[C:6]([CH3:27])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 178496984HCID 178496984, compound

Product 1

HCID 178428514HCID 178428514, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under inert atmosphere to a solution of methyl 2-((2-chloro-4-methylpyridin-3-yl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (Intermediate-48, 0.200 g, 0.516 mmol) in dry toluene was added 3-trifluoromethyl aniline (0.124 g, 0.774 mmol) and trimethyl aluminium (2.0 M solution in toluene) (0.037 g, 0.516 mmol). The reaction mixture was refluxed for 1 h. The reaction mass was quenched in water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated. The obtained crude product was purified by column chromatography on neutral alumina eluting with 40.0% Acetone: petroleum ether to afford 0.150 g of the desired product. 1HNMR (DMSO-d6): δ 1.56 (s, 6H), 2.24 (s, 3H), 3.08 (s, 2H), 7.45-7.37 (m, 3H), 7.59 (t, J=7.8 Hz, 1H), 7.72 (d, J=8.4 Hz, 1H), 8.15 (d, J=4.2 Hz, 1H), 8.33 (s, 1H), 9.93 (s, 1H), 11 (bs, 1H); MS [M+H]+: 516.35.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. customThe reaction mass was quenched in water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. customwas purified by column chromatography on neutral alumina eluting with 40.0% Acetone

Sources & evidence

ORD record
ord-2d7ed7303fe641e29dc63175bfc9564d
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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