3-(Trifluoromethyl)aniline → HCID 178422751, compound

HRID 1898410Notes

Reaction equation

HRID 1898410 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][NH:5][C:6]1[NH:10][C:9]2[C:11]3[CH2:12][C:13]([CH3:23])([CH3:22])[O:14][C:15]=3[C:16]([C:18]([O:20]C)=O)=[CH:17][C:8]=2[N:7]=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[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][NH:5][C:6]1[NH:10][C:9]2[C:11]3[CH2:12][C:13]([CH3:22])([CH3:23])[O:14][C:15]=3[C:16]([C:18]([NH:33][C:32]3[CH:34]=[CH:35][CH:36]=[C:30]([C:29]([F:28])([F:37])[F:38])[CH:31]=3)=[O:20])=[CH:17][C:8]=2[N:7]=1

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 178497000HCID 178497000, compound

Product 1

HCID 178422751HCID 178422751, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-137 using methyl 2-((2-chlorobenzyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (Intermediate-52, 0.200 g, 0.519 mmol), 3-trifluoromethyl aniline (0.167 g, 1.038 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL) and dry toluene (5.0 mL). The obtained crude was purified by column chromatography eluting with 0.5% DCM:MeOH to afford 0.0650 g of the desired product. 1HNMR (DMSO-d6): δ 1.57 (s, 6H), 3.16 (s, 2H), 7.00 (d, J=6 Hz, 2H), 7.30-7.42 (m, 2H), 7.44-7.64 (m, 6H), 7.72 (d, J=7.8 Hz, 1H), 8.35 (s, 1H), 9.96 (s, 1H), 10.90 (s, 1H); [M+H]+: 515.19.

Workup

  1. customThe title compound was prepared
  2. customThe obtained crude
  3. customwas purified by column chromatography
  4. washeluting with 0.5% DCM

Sources & evidence

ORD record
ord-3979715b5b0a4b16a83c0642047b500f
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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