4-t-Butylbenzenesulfonyl chloride → 4-tert-butyl-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide

HRID 397275노트

반응식

HRID 397275 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[C:21]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[C:20]([O:31][CH3:32])[N:19]=[C:18]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[N:17]=1>N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:15][C:16]2[C:21]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[C:20]([O:31][CH3:32])[N:19]=[C:18]([C:33]3[N:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[N:17]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 229997224-Amino-6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine

생성물 1

HCID 229997044-tert-butyl-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide수율 3.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

4-tert-Butyl-benzene sulphonyl chloride (286 mg) was added to a stirred solution of 4-amino-6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine (EP 713875A1) (100 mg) in dry pyridine (2 ml) at room temperature and the resulting mixture stirred for 36 hours. The reaction was then partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (10 ml) and the organic phase separated, washed (2N aqueous hydrochloric acid 2×10 ml, water 2×10 ml), dried (MgSO4) and evaporated under reduced pressure. Column chromatography on silica eluting with a solvent gradient of pentane:ethyl acetate 25:75 changing to 0:100, then dichloromethane:methanol 95:5 gave 4-tert-butyl-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide as an off-white coloured solid (5 mg).

후처리

  1. customThe reaction was then partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (10 ml)
  2. customthe organic phase separated
  3. washwashed (2N aqueous hydrochloric acid 2×10 ml, water 2×10 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b9c55d95b4d949b8b8f09fb1262a142b
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610518B2

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