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Ammonium Chloride → Carbamic acid, N-[4-chloro-5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]hydroxymethyl]-2-thiazolyl]-, 1,1-dimethylethyl ester

HRID 509933
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HRID 509933 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[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:26]([O:30][C:31](=[O:41])[NH:32][C:33]1[S:34][C:35]([CH:39]=[O:40])=[C:36]([Cl:38])[N:37]=1)([CH3:29])([CH3:28])[CH3:27].[Cl-].[NH4+]>O1CCCC1>[C:26]([O:30][C:31](=[O:41])[NH:32][C:33]1[S:34][C:35]([CH:39]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([Cl:19])[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:40])=[C:36]([Cl:38])[N:37]=1)([CH3:29])([CH3:27])[CH3:28]
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HCID 25517Ammonium ChlorideHCID 242292391-Benzenesulfonyl-5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridineHCID 45117878Tert-butyl (4-chloro-5-formylthiazol-2-yl)carbamate2회HCID 178418918HCID 178418918, 화합물2회

생성물 1

HCID 57619425Carbamic acid, N-[4-chloro-5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]hydroxymethyl]-2-thiazolyl]-, 1,1-dimethylethyl ester
수율 60.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-25 °C

실험 절차

To a solution of 1-benzenesulfonyl-5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (12, 4.40 g, 10.5 mmol) in 30.0 mL of tetrahydrofuran at −45° C. under nitrogen, a solution of isopropylmagnesium chloride (5.4 mL, 2.0 M in tetrahydrofuran) was added slowly over 10 minutes. The reaction was allowed to warm to −25° C. over 30 minutes, then cooled to −65° C., followed by adding the cold deprotonated (4-chloro-5-formyl-thiazol-2-yl)-carbamic acid tert-butyl ester, which was prepared in situ by adding isopropylmagnesium chloride (5.0 mL, 2.0 M in tetrahydrofuran) to (4-chloro-5-formyl-thiazol-2-yl)-carbamic acid tert-butyl ester (26, 2.51 g, 9.55 mmol) in 23.0 mL of tetrahydrofuran at −78° C. under nitrogen. The reaction was allowed to warm to room temperature over 2 hours, then poured into aqueous ammonium chloride, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 25-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (27, 3.70 g, 60.3%). MS (ESI) [M+H+]+=554.2.

후처리

  1. temperaturecooled to −65° C.
  2. customwas prepared in situ
  3. temperatureto warm to room temperature over 2 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with 25-100% ethyl acetate in hexane
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-089815ed2f214dc18103f47882d48eab
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096593B2

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