Citric Acid → Benzylsulfamic acid [6-chloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide

HRID 1181241노트

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HRID 1181241 반응식
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([S:18][CH3:19])[N:3]=1.[K].[CH2:21]([NH:28][S:29](=[O:32])(=[O:31])[NH2:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[Cl:17][C:6]1[N:5]=[C:4]([S:18][CH3:19])[N:3]=[C:2]([NH:30][S:29](=[O:31])(=[O:32])[NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 219795924,6-Dichloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidineHCID 68727905Benzylsulfamic acid amide potassium salt

생성물 1

HCID 21041378Benzylsulfamic acid [6-chloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide수율 79.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
0 °C

실험 절차

4,6-Dichloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidine (1.5 g) was dissolved in DMSO (30 ml) and benzylsulfamic acid amide potassium salt (2.12 g, Referential Example 22) was added. Stirring was continued for 18 h. The reaction mixture was poured onto water, acidified by solid citric acid (1.9 g), cooled to 0° C. and the precipitate was filtered off and purified by column chromatography over silica gel with hexane/EtOAc=2/1 to give benzylsulfamic acid [6-chloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide (1.75 g) as a white powder. LC-MS: tR=5.27; [M+H]+=467.04.

후처리

  1. additionThe reaction mixture was poured onto water
  2. filtrationthe precipitate was filtered off
  3. custompurified by column chromatography over silica gel with hexane/EtOAc=2/1

출처 및 근거

ORD 기록
ord-a28d9f338a7c48bab0854162568b9e84
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285549B2

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