Piperazine → HCID 9858707、化合物

HRID 1793852ノート

反応式

HRID 1793852 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1F.C(=O)([O-])[O-].[K+].[K+].[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1

参加物

4

反応物 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 11334553HCID 11334553、化合物

生成物 1

HCID 9858707HCID 9858707、化合物収率 93%

実験手順

A mixture of (5RS)-3-(3,4-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-4,5-dihydroisoxazole (528 mg, 2 mM), potassium carbonate (414 mg, 3 mM), and piperazine (7.5 g) was heated under nitrogen at 130° for 4 hours. After cooling, the mixture was partitioned between water (150 ml) and ethyl acetate (150 ml). The organic extract was washed with sodium bicarbonate (75 ml), and brine (75 ml). After drying (magnesium sulfate) and evaporation, the desired product (614 mg) was obtained sufficiently pure without chromatography. MS (ESP): 331 (MH+) for C16H19FN6O NMR (DMSO-d6) δ: 2.81 (t, 4H); 2.97 (t, 4H); 3.20 (dd overlapped by H2O, 1H); 3.52 (dd, 1H); 4.58 (dd, 1H); 4.64 (dd, 1H); 5.08 (m, 1H); 7.02 (t, 1H); 7.30 (overlapping m, 2H); 7.70 (d, 1H); 8.11 (d, 1H); NH missing—exchanged.

後処理

  1. temperaturewas heated under nitrogen at 130° for 4 hours
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between water (150 ml) and ethyl acetate (150 ml)
  4. extractionThe organic extract
  5. washwas washed with sodium bicarbonate (75 ml), and brine (75 ml)
  6. customAfter drying
  7. custom(magnesium sulfate) and evaporation

出典と根拠

ORDレコード
ord-27972a76efd4450da10761270248a017
出典データセット
uspto-grants-2006_04
特許番号
US07022705B2

反応ノート

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