3-(Trifluoromethyl)aniline → HCID 67503683, compound

HRID 1898479Notes

Reaction equation

HRID 1898479 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]([F:39])([F:38])[C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34].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:34][C:33]3[CH:35]=[CH:36][CH:37]=[C:31]([C:30]([F:29])([F:38])[F:39])[CH:32]=3)=[O:24])=[CH:21][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 73753-(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 67503683HCID 67503683, compoundYield 38.3%

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, 0.237 mmol), 3-(trifluoromethyl) aniline (0.057 g, 0.356 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL), dry toluene (5.0 mL) to afford 0.050 g of the desired product. 1HNMR (DMSO-d6): δ 1.61 (s, 6H), 3.49 (s, 2H), 3.59 (s, 3H), 7.24 (s, 1H), 7.45 (d, J=7.8 Hz, 1H), 7.59 (t, J=7.8 Hz, 1H), 7.78 (d, J=8.4 Hz, 1H), 8.31 (s, 1H), 8.47 (s, 2H), 9.90 (s, 1H), 10.91 (s, 1H); MS [M]+: 550.11.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0da28a40c03d4d8692717b055e57cbf4
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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