Phosphorus oxychloride → 4-Chloro-1-[2-(4-methylpiperazin-1-yl)ethyl]-5-phenyl-3-pyrrolidin-1-yl-pyrazolo[3,4-c]pyridazine

HRID 588582ノート

反応式

HRID 588582 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:14]3[N:15]=[N:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:18](O)[C:13]=3[C:12]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:11]2)[CH2:4][CH2:3]1.O=P(Cl)(Cl)[Cl:33]>C(Cl)Cl>[Cl:33][C:18]1[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:16][N:15]=[C:14]2[N:10]([CH2:9][CH2:8][N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[N:11]=[C:12]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:13]=12

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178480892HCID 178480892、化合物

生成物 1

HCID 867172834-Chloro-1-[2-(4-methylpiperazin-1-yl)ethyl]-5-phenyl-3-pyrrolidin-1-yl-pyrazolo[3,4-c]pyridazine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

A suspension of 1-[2-(4-methylpiperazin-1-yl)ethyl]-5-phenyl-3-pyrrolidin-1-yl-pyrazolo[3,4-c]pyridazin-4-ol (90 mg) in POCl3 (6 mL) and CH2Cl2 (3 mL) was heated to 60° C. for 2.5 h. The mixture was concentrated in vacuo and the residue was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The layers were separated and the aqueous was extracted with CH2Cl2, the combined organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by preparative HPLC to provide Compound Iz (12 mg).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with CH2Cl2
  5. dry with materialthe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative HPLC
  9. customto provide Compound Iz (12 mg)

出典と根拠

ORDレコード
ord-97be80fc7468443ea8873da1bb30e91d
出典データセット
uspto-grants-2016_01
特許番号
US09227976B2

反応ノート

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