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

HRID 10259노트

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HRID 10259 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-fbd7d5ace7f143329a76ff9d61c40004
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094781B2

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