Hydrochloric Acid → 1-({[2-(Benzylthio)-6-chloropyrimidin-4-yl]amino}sulfonyl)-N,N-dimethyl-D-prolinamide

HRID 424664Notes

Reaction equation

HRID 424664 reaction equation
[H-].[Na+].[NH2:3][S:4]([N:7]1[CH2:16][CH2:15][CH2:14][C@@H:8]1[C:9]([N:11]([CH3:13])[CH3:12])=[O:10])(=[O:6])=[O:5].[CH2:17]([S:24][C:25]1[N:30]=[C:29](NS(C)(=O)=O)[CH:28]=[C:27](NCCO)[N:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[ClH:40]>CN(C=O)C>[CH2:17]([S:24][C:25]1[N:30]=[C:29]([NH:3][S:4]([N:7]2[CH2:16][CH2:15][CH2:14][C@@H:8]2[C:9]([N:11]([CH3:13])[CH3:12])=[O:10])(=[O:6])=[O:5])[CH:28]=[C:27]([Cl:40])[N:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 57833129N-{2-(Benzylthio)-6-[(2-hydroxyethyl)amino]pyrimidin-4-yl}methanesulfonamideHCID 667020511-(Aminosulfonyl)-N,N-dimethyl-D-prolinamide

Product 1

HCID 866398311-({[2-(Benzylthio)-6-chloropyrimidin-4-yl]amino}sulfonyl)-N,N-dimethyl-D-prolinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% Sodium hydride (0.42 g) was added to a solution of the subtitle product of step iii) (1.50 g) in DMF (20 ml) at 0° C. This mixture was stirred for 1 h and then a solution of the subtitle product of Example 19 step (1.60 g) in DMF (5 ml) was added dropwise. The mixture was allowed to reach room temperature and stirred there for 2 days. To the mixture was added aqueous hydrochloric acid (100 ml) and the resulting precipitate was filtered. This solid was then stirred with EtOAc (200 ml) and filtered to afford the subtitle compound as a solid. Yield: 2.0 g.

Workup

  1. customto reach room temperature
  2. stirringstirred there for 2 days
  3. filtrationthe resulting precipitate was filtered
  4. stirringThis solid was then stirred with EtOAc (200 ml)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d4a4f5c0daca464e8cd7645920ff4bbf
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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