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

HRID 1898483Notes

Reaction equation

HRID 1898483 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:28])[C:7]=1[NH:8][C:9]1[N:13]([CH3:14])[C:12]2[C:15]3[CH2:16][C:17]([CH3:27])([CH3:26])[O:18][C:19]=3[C:20]([C:22]([O:24]C)=O)=[CH:21][C:11]=2[N:10]=1.[F:29][C:30]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:31]=1[NH2:32].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:28][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9]1[N:13]([CH3:14])[C:12]2[C:15]3[CH2:16][C:17]([CH3:27])([CH3:26])[O:18][C:19]=3[C:20]([C:22]([NH:32][C:31]3[CH:33]=[C:34]([C:37]([F:38])([F:39])[F:40])[CH:35]=[CH:36][C:30]=3[F:29])=[O:24])=[CH:21][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 67502200Methyl 2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate

Product 1

HCID 866647122-((3,5-Dichloropyridin-4-yl)amino)-N-(2-fluoro-5-(trifluoromethyl)phenyl)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamideYield 34.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-143 by using methyl 2-((3,5-dichloropyridin-4-yl)amino)-1,7,7-trimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (Intermediate-60, 0.100 g, 0.245 mmol), 2-fluoro-5-(trifluoromethyl)aniline (0.065 g, 0.363 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL), dry toluene (5.0 mL) to afford 0.048 g of the desired product. 1HNMR (DMSO-d6): δ 1.60 (s, 6H), 3.52 (s, 2H), 3.60 (s, 3H), 7.29 (s, 1H), 7.53-7.63 (m, 2H), 8.48 (s, 2H), 8.86 (d, J=5.4 Hz, 1H), 10.22 (m, 1H), 10.94 (s, 1H); MS [M]+: 568.08.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-3309712648524351a73a6c1a22cad863
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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