3-(Trifluoromethyl)aniline → HCID 178422752, compound

HRID 1898409Notes

Reaction equation

HRID 1898409 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[C:4]([NH:6][C:7]1[NH:11][C:10]2[C:12]3[CH2:13][C:14]([CH3:24])([CH3:23])[O:15][C:16]=3[C:17]([C:19](OC)=[O:20])=[CH:18][C:9]=2[N:8]=1)=[O:5].[F:30][C:31]([F:40])([F:39])[C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[C:4]([NH:6][C:7]1[NH:11][C:10]2[C:12]3[CH2:13][C:14]([CH3:24])([CH3:23])[O:15][C:16]=3[C:17]([C:19]([NH:35][C:34]3[CH:36]=[CH:37][CH:38]=[C:32]([C:31]([F:30])([F:39])[F:40])[CH:33]=3)=[O:20])=[CH:18][C:9]=2[N:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 178497001HCID 178497001, compound

Product 1

HCID 178422752HCID 178422752, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by following the procedure as described for Example-137 using methyl 2-(2-chloro-6-fluorobenzamido)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (Intermediate-51, 0.200 g, 0.477 mmol), 3-trifloromethyl aniline (0.230 g, 1.43 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL) and dry toluene (5.0 mL). The reaction mass was stirred at RT for 4-5 h. The obtained crude was purified on preparative TLC using 4% DCM:MeOH as solvent system to afford 0.011 g of the desired product. 1HNMR (DMSO-d6): δ 1.57 (s, 6H), 3.14 (s, 2H), 6.30 (s, 1H), 7.43 (d, J=7.8 Hz, 2H), 7.56-7.70 (m, 4H), 7.86 (q, J=6.3 Hz, 1H), 8.15 (bs, 2H), 9.71 (s, 1H); MS [M+H]+: 547.06.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude
  3. customwas purified on preparative TLC

Sources & evidence

ORD record
ord-a3f690e728ce4ff09b0b1140a281c784
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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