Pyridine → HCID 59717043, compound

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13]3[N:14]([CH3:30])[C:15](=[O:29])[CH:16]=[C:17]([O:18][S:19]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:12]=3[C:11](=[O:31])[N:10]([CH:32]3[CH2:34][CH2:33]3)[C:9]2=[O:35])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)(Cl)Cl>[CH:32]1([N:10]2[C:11](=[O:31])[C:12]3[C:17]([O:18][S:19]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)(=[O:21])=[O:20])=[CH:16][C:15](=[O:29])[N:14]([CH3:30])[C:13]=3[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:43]([CH3:42])(=[O:45])=[O:44])[CH:3]=3)[C:9]2=[O:35])[CH2:33][CH2:34]1

Participants

Procedure

To toluene-4-sulfonic acid 1-(3-aminophenyl)-3-cyclopropyl-8-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 13 (5 g) obtained in Step 7 was added pyridine (40 ml), a solution of methanesulfonyl chloride 14 (0.9 ml) in chloroform (10 ml) was added dropwise with stirring under ice-cooling, and the mixture was stirred for 3 hrs in an ice bath. The reaction mixture was concentrated under reduced pressure, 2N hydrochloric acid was added and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant solid was suspended in diethyl ether:hexane=1:1, and filtered by suction to give toluene-4-sulfonic acid 3-cyclopropyl-1-(3-methanesulfonylaminophenyl)-8-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 15 (5.5 g, 95%) as a white solid.