Hexane → HCID 46215810、化合物

HRID 2367176ノート

反応式

HRID 2367176 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1.O.[NH2:26][NH2:27].CCOC(C)=O.CCCCCC>CCO>[NH2:13][C:12]1[C:11]2[C:10](=[CH:9][C:8]([C:6]3[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:27][N:26]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 58504409HCID 58504409、化合物

生成物 1

HCID 46215810HCID 46215810、化合物収率 39.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
100 °C

実験手順

To 4-{2-amino-6-[(phenylmethyl)amino]-4-pyrimidinyl}-2-fluorobenzonitrile (367 mg, 1.15 mmol) in EtOH (10 mL) was added hydrazine monohydrate (1.0 mL, 20.4 mmol) and the reaction mixture was stirred overnight at 100° C. The mixture was poured onto water and EtOAc. The layers were separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford crude product (280 mg). This material was dissolved in EtOH. Hexane was added until a precipitate began to form (a spatula was used to scratch the walls). The mixture was decanted and the solid was dried under vacuum to afford the title compound (150 mg, 39%) as a tan solid. LC-MS (ES) m/z=332 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 4.59 (s, 2H), 6.29 (s, 1H), 7.23 (m, 1H), 7.28-7.38 (m, 4H), 7.41 (d, J=8.3 Hz, 1H), 7.72 (d, J=8.6 Hz, 1H), 7.75 (s, 1H).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford crude product (280 mg)
  8. customto form (a spatula
  9. customThe mixture was decanted
  10. customthe solid was dried under vacuum

出典と根拠

ORDレコード
ord-c1e7a20566dc488c841f9522fc5950d7
出典データセット
uspto-grants-2014_04
特許番号
US08697685B2

反応ノート

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