Ammonium Chloride → HCID 68739481, 화합물

HRID 240757노트

반응식

HRID 240757 반응식
CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[CH:9]2)=[O:5].[CH2:16]([Mg]Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1>[NH:11]1[C:12]2[C:8](=[CH:7][C:6]([C:4](=[O:5])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][CH:13]=2)[CH:9]=[N:10]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 62814299N-methoxy-N-methyl-1H-indazole-5-carboxamideHCID 178418336HCID 178418336, 화합물3회

생성물 1

HCID 68739481HCID 68739481, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of Example 75B (900 mg, 4.39 mmol) in tetrahydrofuran (10 mL) was cooled under argon with an ice bath and treated with a 2M solution of benzyl magnesium chloride in tetrahydrofuran (6.6 mL, 13.16 mmol). The reaction was stirred overnight at room temperature followed by the addition of one more equivalent of benzyl magnesium chloride. The mixture was heated at 70° C. for 9 hours. One more equivalent of benzylmagnesium chloride was added, and the reaction was heated at 70° C. for another 90 minutes and was allowed to cool to room temperature. Aqueous saturated ammonium chloride was added, and the product was extracted with ethyl acetate and purified by silica gel column chromatography using 30% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 237.1 (M+H)+.

후처리

  1. temperatureThe mixture was heated at 70° C. for 9 hours
  2. temperaturethe reaction was heated at 70° C. for another 90 minutes
  3. temperatureto cool to room temperature
  4. extractionthe product was extracted with ethyl acetate
  5. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0869cf7e01dc41c8aa2a73e061bf4444
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648069B2

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