4-(Trifluoromethyl)aniline → HCID 178432348, compound

HRID 1898443Notes

Reaction equation

HRID 1898443 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23](O)=[O:24])=[CH:13][C:12]=2[N:11]=1.S(Cl)(Cl)=O.[F:30][C:31]([F:40])([F:39])[C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1.[H-].[Na+]>C1COCC1.C1C=CC=CC=1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[NH:22][C:21]2[C:16]3[N:17]=[C:18]([CH3:20])[O:19][C:15]=3[C:14]([C:23]([NH:36][C:35]3[CH:37]=[CH:38][C:32]([C:31]([F:30])([F:39])[F:40])=[CH:33][CH:34]=3)=[O:24])=[CH:13][C:12]=2[N:11]=1

Participants

7

Reactant 4

HCID 99644-(Trifluoromethyl)anilineHCID 24386Thionyl ChlorideHCID 24758Sodium hydrideHCID 178432356HCID 178432356, compound

Product 1

HCID 178432348HCID 178432348, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-177 using 7-[(2,6-dichlorophenyl)amino]-2-methyl-8H-imidazo[4,5-e][1,3]benzoxazole-4-carboxylic acid (Intermediate-55, 0.100 g, 0.276 mmol), benzene (4 mL), thionyl chloride (5.0 mL), 4-(trifluoro methyl) aniline (0.133 g, 0.828 mmol), THF (5.0 mL) and 60% NaH (0.033 g, 0.825 mmol). The obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH:DCM to afford 0.018 g of the desired product. 1HNMR (DMSO-d6): δ 2.72 (s, 3H), 7.41 (s, 2H), 7.63 (s, 2H), 7.73 (d, J=8.4 Hz, 2H), 8.00 (d, J=8.4 Hz, 2H), 9.47 (s, 1H), 11.39 (s, 1H), 11.60 (s, 1H); MS [M+H]+: 520.39.

Workup

  1. customThe title compound was prepared
  2. customThe obtained product was further purified by column chromatography on neutral alumina eluting with 1.5-2.0% MeOH

Sources & evidence

ORD record
ord-3e510a84b4184adcad7fcdedfa7e4a1d
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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