Pyridine → HCID 136375759, compound

HRID 869266Notes

Reaction equation

HRID 869266 reaction equation
Cl.Cl.[CH:3]([S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[N:17]=[C:18]([NH:26][CH:27]2[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]2)[NH:19][C:20](=[O:25])[C:21]=1[C:22]([NH2:24])=[O:23])(=[O:8])=[O:7])([CH3:5])[CH3:4].N1C=CC=CC=1.[S:39](Cl)([CH3:42])(=[O:41])=[O:40]>C(O)C>[CH:3]([S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[N:17]=[C:18]([NH:26][CH:27]2[CH2:32][CH2:31][CH2:30][N:29]([S:39]([CH3:42])(=[O:41])=[O:40])[CH2:28]2)[NH:19][C:20](=[O:25])[C:21]=1[C:22]([NH2:24])=[O:23])(=[O:8])=[O:7])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 136375765HCID 136375765, compound

Product 1

HCID 136375759HCID 136375759, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-{[2-(isopropylsulfonyl)phenyl]amino}-6-oxo-2-(piperidin-3-ylamino)-1,6-dihydropyrimidine-5-carboxamide dihydrochloride (Example 29) (67 mg) and pyridine (1.3 mL), mesyl chloride (0.10 mL) was added under ice cooling and stirred for 1 hour. After ethanol was added to the reaction system, the reaction system was concentrated. The resulting residue was partitioned using chloroform and saturated aqueous sodium hydrogen carbonate, and the organic layer was dried. The organic layer was concentrated, followed by an azeotropic process with toluene. The resulting residue was solidified with ethyl acetate-hexane. The resulting solid was recrystallized from ethanol to give 4-{[2-(isopropylsulfonyl)phenyl]amino}-2-{[1-(methylsulfonyl)piperidin-3-yl]amino}-6-oxo-1,6-dihydropyrimidine-5-carboxamide (43 mg).

Workup

  1. additionwas added under ice cooling
  2. concentrationthe reaction system was concentrated
  3. customThe resulting residue was partitioned
  4. customthe organic layer was dried
  5. concentrationThe organic layer was concentrated
  6. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-96257634980440c9943de906057a9535
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

Loading…