Hydrochloric Acid → 2-(4-chloro-3-(4-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acid

HRID 1775573ノート

反応式

HRID 1775573 の反応式
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[N:10]([CH2:11][C:12]([OH:14])=[O:13])[N:9]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[ClH:30]>>[Cl:30][C:22]1[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:1][N:5]=[C:6]2[N:10]([CH2:11][C:12]([OH:14])=[O:13])[N:9]=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:7]=12

参加物

4

反応物 3

HCID 313Hydrochloric Acid2 回HCID 23668193Sodium NitriteHCID 709836262-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)acetic acid

生成物 1

HCID 709821902-(4-chloro-3-(4-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acid

反応条件

温度
-5 °C

実験手順

To a cooled (cooling bath −5° C.) stirred suspension of sodium nitrite (320 mg, 4.65 mmol) in conc. HCl (5 mL) was added 2-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)acetic acid (521 mg, 1.55 mmol). A further 5 ml of conc. HCl was added and the cooling bath was removed and the reaction mixture was stirred at room temperature for 3.5 h. Water and CH2Cl2 were added to the reaction mixture. The aqueous phase was extracted with CH2Cl2 and the organic phases combined, dried over MgSO4, filtered and evaporated to give 2-(4-chloro-3-(4-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)acetic acid as a solid (419 mg), which was used as such in the subsequent step.

後処理

  1. temperatureTo a cooled
  2. customthe cooling bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 3.5 h
  4. additionWater and CH2Cl2 were added to the reaction mixture
  5. extractionThe aqueous phase was extracted with CH2Cl2
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-a68c259d6827475d9db174fc464967a2
出典データセット
uspto-grants-2016_02
特許番号
US09260381B2

反応ノート

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