Benzylsulfamic acid [5-(2-chloro-5-methoxy-phenoxy)-6-(2-hydroxy-ethoxy) pyrimidin-4-yl]-amide → Benzylsulfamic acid [6-[2-(5-methylsulfanyl-pyrimidin-2-yloxy)ethoxy]-5-(2-chloro-5-methoxy-phenoxy)pyrimidin-4-yl]-amide

HRID 1181249Notes

Reaction equation

HRID 1181249 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:3]=1[O:4][C:5]1[C:6]([NH:15][S:16](=[O:26])(=[O:25])[NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:7][CH:8]=[N:9][C:10]=1[O:11][CH2:12][CH2:13][OH:14].[CH3:33][S:34][C:35]1[CH:36]=[N:37][C:38](Cl)=[N:39][CH:40]=1>>[CH3:33][S:34][C:35]1[CH:36]=[N:37][C:38]([O:14][CH2:13][CH2:12][O:11][C:10]2[N:9]=[CH:8][N:7]=[C:6]([NH:15][S:16](=[O:26])(=[O:25])[NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]=2[O:4][C:3]2[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:2]=2[Cl:1])=[N:39][CH:40]=1

Participants

3

Reactant 2

HCID 21041229Benzylsulfamic acid [5-(2-chloro-5-methoxy-phenoxy)-6-(2-hydroxy-ethoxy) pyrimidin-4-yl]-amideHCID 219795322-Chloro-5-(methylthio)pyrimidine

Product 1

HCID 21979560Benzylsulfamic acid [6-[2-(5-methylsulfanyl-pyrimidin-2-yloxy)ethoxy]-5-(2-chloro-5-methoxy-phenoxy)pyrimidin-4-yl]-amideYield 45.7%

Procedure

Benzylsulfamic acid [6-[2-(5-methylsulfanyl-pyrimidin-2-yloxy)-ethoxy]-5-(2-chloro-5-methoxy-phenoxy)-pyrimidin-4-yl]-amide (138 mg) (Example 213) was prepared from benzylsulfamic acid [5-(2-chloro-5-methoxy-phenoxy)-6-(2-hydroxy-ethoxy)-pyrimidin-4-yl]-amide (240 mg) (Example 211) and 5-methylsulfanyl-2-chloropyrimidine (180 mg) according to the procedure described in Example 14. LC-MS: tR=5.22; [M+H]+=606.75.

Sources & evidence

ORD record
ord-83840815539646c5a7367acf5cd387fb
Source dataset
uspto-grants-2007_10
Patent number
US07285549B2

Reaction notes

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