tert-butyl ({4-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyanophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate → 4-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyano-N-1,3-thiazol-4-ylbenzenesulfonamide

HRID 1401921노트

반응식

HRID 1401921 반응식
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]([C:10]3[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:11]=3[O:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([N:22]([C:30]4[N:31]=[CH:32][S:33][CH:34]=4)C(=O)OC(C)(C)C)(=[O:21])=[O:20])=[CH:15][C:14]=3[C:35]#[N:36])=[CH:8][CH:7]=[N:6]2)[CH2:2]1>Cl.O1CCOCC1>[NH:1]1[CH2:2][CH:3]([N:5]2[C:9]([C:10]3[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:11]=3[O:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:30]4[N:31]=[CH:32][S:33][CH:34]=4)(=[O:21])=[O:20])=[CH:15][C:14]=3[C:35]#[N:36])=[CH:8][CH:7]=[N:6]2)[CH2:4]1

참가 물질

4

반응물 1

HCID 59436550tert-butyl ({4-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyanophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate

생성물 1

HCID 574948254-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyano-N-1,3-thiazol-4-ylbenzenesulfonamide수율 38.9%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

tert-butyl ({4-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyanophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate (Preparation 679, 200 mg, 0.326 mmol) was stirred in 4M hydrogen chloride solution in 1,4-dioxan (10 ml) at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between methyl-t-butyl ether (80 ml) and water (40 ml). The aqueous layer was neutralized to pH=7 by adding sodium hydrogen carbonate and was then concentrated in vacuo. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.880 aqueous ammonia, 90:10:1 to 70:30:3. This gave a buff powder (65 mg) which was triturated with methyl tert-butyl ether to give the title compound as a buff powder, 55 mg.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between methyl-t-butyl ether (80 ml) and water (40 ml)
  3. additionby adding sodium hydrogen carbonate
  4. concentrationwas then concentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-cb607c60cf9a421d885f467f43251084
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08907101B2

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