2,2,2-Trifluoroethanol → 4-(1H-indol-3-yl)-N-[2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrophenyl]pyrimidin-2-amine

HRID 1842725

反応式

HRID 1842725 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([NH:18][C:19]2[N:24]=[C:23]([C:25]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[NH:27][CH:26]=3)[CH:22]=[CH:21][N:20]=2)=[C:11]([O:34][CH3:35])[CH:10]=1.C(O)C(F)(F)F>>[NH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:25]([C:23]2[CH:22]=[CH:21][N:20]=[C:19]([NH:18][C:12]3[CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:9]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:10][C:11]=3[O:34][CH3:35])[N:24]=2)=[CH:26]1

参加物

4

反応物 3

HCID 64092,2,2-TrifluoroethanolHCID 531671-MethylpiperazineHCID 71240865N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1H-indol-3-yl)pyrimidin-2-amine2 回

生成物 1

HCID 712408044-(1H-indol-3-yl)-N-[2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrophenyl]pyrimidin-2-amine収率 33%

反応条件

温度
120 °C

実験手順

A mixture of 1-methylpiperazine (148 mg, 1.48 mmol), N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(1H-indol-3-yl)pyrimidin-2-amine (Intermediate 68, 224 mg, 0.59 mmol) and trifluoroethanol (5 mL) was sealed into a microwave tube and heated to 120° C. for 1 h in a microwave reactor and then cooled to r.t. The mixture was then concentrated in vacuo. Trituration of the resulting brown gum with ethanol and then diethyl ether gave a solid that was collected by filtration and dried under vacuum to give the title compound (89 mg, 33%) as a pale brown solid; 1H NMR: 3.02-3.13 (4H, m), 4.00 (3H, s), 6.86 (1H, s), 7.08 (1H, t), 7.18 (1H, t), 7.31 (1H, d), 7.45 (1H, d), 8.08 (1H, s), 8.33 (2H, dd), 8.82 (1H, d), 11.81 (1H, s); m/z: ES+ MH+ 460.5.

後処理

  1. customwas sealed into a microwave tube
  2. temperaturecooled to r.t
  3. concentrationThe mixture was then concentrated in vacuo
  4. customTrituration of the resulting brown gum with ethanol and then diethyl ether gave a solid
  5. filtrationthat was collected by filtration
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-f073852175c34125b6068b70755260c7
出典データセット
uspto-grants-2015_02
特許番号
US08946235B2

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