2-Fluoro-4-(trifluoromethyl)aniline → 2-((3,5-Dichloropyridin-4-yl)amino)-N-(2-fluoro-4-(trifluoromethyl)phenyl)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide

HRID 1898459Notes

Reaction equation

HRID 1898459 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23]([O:25]C)=O)=[CH:14][C:12]=2[N:13]=1.[F:28][C:29]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:30]=1[NH2:31].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:27][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23]([NH:31][C:30]3[CH:32]=[CH:33][C:34]([C:36]([F:37])([F:38])[F:39])=[CH:35][C:29]=3[F:28])=[O:25])=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 27376742-Fluoro-4-(trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 178496992HCID 178496992, compound

Product 1

HCID 1784227652-((3,5-Dichloropyridin-4-yl)amino)-N-(2-fluoro-4-(trifluoromethyl)phenyl)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 36.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-137 by using methyl 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylate (Step-1 of Intermediate-3, 0.100 g, 0.245 mmol), 2-fluoro-4-(trifluoromethyl)aniline (0.064 g, 0.357 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL), dry toluene (5.0 mL) at room temperature to afford 0.050 g of the desired product. 1HNMR (DMSO-d6): δ 1.57 (s, 6H), 3.11 (s, 2H), 7.31 (s, 1H), 7.62 (d, J=8.1 Hz, 1H), 7.81 (d, J=11.4 Hz, 1H), 8.46 (s, 2H), 8.70 (t, J=8.4 Hz, 1H), 10.23 (s, 1H), 11.03 (br s, 1H), 11.60 (br s, 1H); MS [M+H]+: 552.33.

Workup

  1. customThe title compound was prepared
  2. customat room temperature

Sources & evidence

ORD record
ord-f1f7e742c7ea4a398519e3212b0ce8c2
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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