4,6-Dichloropyrimidine → N-{3-[1-(6-chloro-pyrimidin-4-yl)-1H-imidazol-2-ylamino]-4-methyl-phenyl}-3-trifluoromethyl-benzamide

HRID 19495

反応式

HRID 19495 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]1[CH:8]=[C:9]([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[CH:10]=[CH:11][C:12]=1[CH3:13].[Cl:27][C:28]1[CH:33]=[C:32](Cl)[N:31]=[CH:30][N:29]=1.C(N(CC)C(C)C)(C)C>CC(O)CC>[Cl:27][C:28]1[N:29]=[CH:30][N:31]=[C:32]([N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[NH:6][C:7]2[CH:8]=[C:9]([NH:14][C:15](=[O:26])[C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)[CH:10]=[CH:11][C:12]=2[CH3:13])[CH:33]=1

参加物

5

反応物 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 58973096N-[3-(1H-Imidazol-2-ylamino)-4-methyl-phenyl]-3-trifluoromethyl-benzamide

生成物 1

HCID 58973058N-{3-[1-(6-chloro-pyrimidin-4-yl)-1H-imidazol-2-ylamino]-4-methyl-phenyl}-3-trifluoromethyl-benzamide

試薬・触媒・溶媒 1

HCID 6568(+-)-2-Butanol溶媒

反応条件

温度
110 °C

実験手順

A mixture of N-[3-(1H-Imidazol-2-ylamino)-4-methyl-phenyl]-3-trifluoromethyl-benzamide (330 mg, 0.92 mmol), 4,6-dichloropyrimidine (409 mg, 2.75 mmol), N,N-diisopropylethyl amine (500 μL, 2.87 mmol) in 2-butanol (20 mL) is heated at 110° C. After 16 hours, the reaction mixture is concentrated. The solid is washed with saturated sodium carbonate, water, ethyl acetate, and dried to give the title compound. 1H NMR 600 MHz (DMSO-d6) δ 10.71 (s, 1H), 10.50 (s, 1H), 9.09 (s, 1H), 8.80 (s, 1H), 8.33 (s, 1H), 8.29 (d, J=7.8 Hz, 1H), 8.17 (s, 1H), 7.96 (d, J=8.4 Hz, 1H), 7.84 (s, 1H), 7.77 (t, J=8.4 Hz, 1H), 7.42 (d, J=7.2 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 6.95 (s, 1H), 2.38 (s, 3H); MS m/z 473.3 (M+1).

後処理

  1. concentrationthe reaction mixture is concentrated
  2. washThe solid is washed with saturated sodium carbonate, water, ethyl acetate
  3. customdried

出典と根拠

ORDレコード
ord-ca0b4baae053415c9b2d4bcefe18a839
出典データセット
uspto-grants-2010_06
特許番号
US07745437B2

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