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

HRID 1525442노트

반응식

HRID 1525442 반응식
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[N:10]([CH2:11][CH2:12]O)[N:9]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:7]=1[C:21]#[C:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH2:29].C(Cl)Cl.[ClH:33]>>[Cl:33][C:21]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:1][N:5]=[C:6]2[N:10]([CH2:11][CH2:12][OH:29])[N:9]=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:7]=12

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 23668193Sodium NitriteHCID 709836322-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanol

생성물 1

HCID 665761762-(4-chloro-3-(4-fluorophenyl)-5-phenyl-1H-pyrazolo[3,4-c]pyridazin-1-yl)ethanol

반응 조건

온도
-10 °C

실험 절차

To a cooled (cooling bath −10° C.) stirred suspension of sodium nitrite (120 mg, 1.7 mmol) in conc. HCl (3.6 mL) was added 2-(5-amino-3-(4-fluorophenyl)-4-(phenylethynyl)-1H-pyrazol-1-yl)ethanol (183 mg, 0.57 mmol) and the reaction mixture was allowed to warm to ambient temperature over 90 min. Water and CH2Cl2 were added to the reaction mixture. The aqueous phase was extracted with CH2Cl2 (×4) and the organic phases combined, dried over MgSO4, filtered and evaporated the crude material was purified using chromatography (silica gel, gradient 20 to 100% ethyl acetate/isohexane) followed by preparative HPLC yielding Compound 77 as a white solid (6.5 mg).

후처리

  1. temperatureTo a cooled
  2. temperatureto warm to ambient temperature over 90 min
  3. extractionThe aqueous phase was extracted with CH2Cl2 (×4)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated the crude material
  7. customwas purified

출처 및 근거

ORD 기록
ord-8948bb0399b64320aeaa298551913c16
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079909B2

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