Pyridine → HCID 59717043, compound

HRID 75633Notes

Reaction equation

HRID 75633 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

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59717362HCID 59717362, compound

Product 1

HCID 59717043HCID 59717043, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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 (5.5 g, 95%) as a white solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hrs in an ice bath
  3. concentrationThe reaction mixture was concentrated under reduced pressure, 2N hydrochloric acid
  4. additionwas added
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. filtrationhexane=1:1, and filtered by suction

Sources & evidence

ORD record
ord-e06c83e928454475b3d5469954384532
Source dataset
uspto-grants-2014_09
Patent number
US08835443B2

Reaction notes

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