Ammonium Chloride → HCID 67201062, 화합물

HRID 509973노트

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HRID 509973 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg]Cl)(C)C.[C:27]([O:31][C:32](=[O:52])[N:33]([CH2:42][C:43]1[C:44]([O:50][CH3:51])=[N:45][CH:46]=[C:47]([F:49])[CH:48]=1)[C:34]1[N:39]=[CH:38][C:37]([CH:40]=[O:41])=[CH:36][N:35]=1)([CH3:30])([CH3:29])[CH3:28].[Cl-].[NH4+]>O1CCCC1>[C:27]([O:31][C:32](=[O:52])[N:33]([C:34]1[N:39]=[CH:38][C:37]([CH:40]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=3)[N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:11]=2)[OH:41])=[CH:36][N:35]=1)[CH2:42][C:43]1[C:44]([O:50][CH3:51])=[N:45][CH:46]=[C:47]([F:49])[CH:48]=1)([CH3:30])([CH3:28])[CH3:29]

참가 물질

6

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HCID 25517Ammonium ChlorideHCID 57963062HCID 57963062, 화합물HCID 591287071H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-methoxy-1-(phenylsulfonyl)-HCID 178418918HCID 178418918, 화합물

생성물 1

HCID 67201062HCID 67201062, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
5 °C

실험 절차

To a solution of 1-benzenesulfonyl-3-iodo-5-methoxy-1H-pyrrolo[2,3-b]pyridine (16, 1 equivalent) in 4.0 mL of tetrahydrofuran, isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 1 equivalent) is added slowly at −50° C. The reaction is allowed to warm to 5° C. over 70 minutes, then cooled to −45° C. and (5-fluoro-2-methoxy-pyridin-3-ylmethyl)-(5-formyl-pyrimidin-2-yl)-carbamic acid tert-butyl ester (123, 0.78 equivalent) in 2.0 mL of tetrahydrofuran is added. The reaction is allowed to warm to room temperature over 1 hour, then poured into aqueous ammonium chloride and extracted with ethyl ether. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound.

후처리

  1. temperaturecooled to −45° C.
  2. temperatureto warm to room temperature over 1 hour
  3. extractionextracted with ethyl ether
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material is purified by silica gel column chromatography
  8. washeluting with 20-100% ethyl acetate in hexane
  9. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-8652c57d4c984a7b93f59de11fd83022
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

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