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

HRID 1181241ノート

反応式

HRID 1181241 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a28d9f338a7c48bab0854162568b9e84
出典データセット
uspto-grants-2007_10
特許番号
US07285549B2

反応ノート

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