Hexane → HCID 46215644、化合物

HRID 2367173ノート

反応式

HRID 2367173 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][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1.O.[NH2:25][NH2:26].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][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:5]=3)=[CH:15][CH:14]=2)[NH:26][N:25]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 513565894-[2-Amino-6-(phenylamino)-4-pyrimidinyl]-2-fluorobenzonitrile

生成物 1

HCID 46215644HCID 46215644、化合物収率 26.3%

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-(phenylamino)-4-pyrimidinyl]-2-fluorobenzonitrile (366 mg, 1.2 mmol) in EtOH (10 mL) was added hydrazine monohydrate (1.0 mL, 32 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 (230 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 (100 mg, 26%) as a tan solid. LC-MS (ES) m/z=302, 304 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 6.51 (s, 1H), 7.04 (m, 1H), 7.32 (m, 2H), 7.46 (dd, J=8.6, 1.3 Hz, 1H), 7.66 (m, 2H), 7.75 (dd, J=8.3, 0.8 Hz, 1H), 7.81 (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 (230 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-de53a9fc66a34927851e63a7a31a8017
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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