3-(Trifluoromethyl)aniline → 4-(3-(2-Chloro-5-(cyclopropanecarboxamidomethyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(trifluoromethyl)phenyl)benzamide

HRID 508978ノート

反応式

HRID 508978 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[C:15]1[NH:19][C:18](=[O:20])[N:17]([C:21]2[CH:30]=[CH:29][C:24]([C:25](OC)=[O:26])=[CH:23][CH:22]=2)[N:16]=1.[F:31][C:32]([F:41])([F:40])[C:33]1[CH:34]=[C:35]([CH:37]=[CH:38][CH:39]=1)[NH2:36].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[CH:4][C:3]=1[C:15]1[NH:19][C:18](=[O:20])[N:17]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([NH:36][C:35]3[CH:37]=[CH:38][CH:39]=[C:33]([C:32]([F:31])([F:40])[F:41])[CH:34]=3)=[O:26])=[CH:23][CH:22]=2)[N:16]=1

参加物

5

反応物 3

HCID 73753-(Trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 136492802methyl 4-(3-(2-chloro-5-(cyclopropane carboxamidomethyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzoate

生成物 1

HCID 1362459744-(3-(2-Chloro-5-(cyclopropanecarboxamidomethyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(trifluoromethyl)phenyl)benzamide収率 7.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

The title compound was prepared by following the procedure as described for Example-31 by using methyl 4-(3-(2-chloro-5-(cyclopropane carboxamidomethyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzoate (Intermediate-42, 0.100 g, 0.24 mmol), 3-(trifluoromethyl)aniline (0.050 g, 0.36 mmol), trimethyl aluminium (2M solution in toluene) (1 mL) and dry toluene (8.0 mL). The reaction mass was quenched in water, extracted with DCM and the organic layer was concentrated to afford 0.010 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.70 (s, 4H), 1.62 (m, 1H), 4.33 (d, J=6.3 Hz, 2H), 7.44-7.67 (m, 4H), 8.10-8.26 (m, 6H), 8.68 (m, 1H), 10.53 (s, 1H), 12.68 (br s, 1H); MS (m/z): 554.30 (M−H)−.

後処理

  1. customThe title compound was prepared
  2. customThe reaction mass was quenched in water
  3. extractionextracted with DCM
  4. concentrationthe organic layer was concentrated

出典と根拠

ORDレコード
ord-91d88cea873a439a8bf54412badf7f41
出典データセット
uspto-grants-2015_08
特許番号
US09096545B2

反応ノート

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