Dimethylamine → HCID 46928898, compound

HRID 2361922Notes

Reaction equation

HRID 2361922 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C@@H:13]2[C:18]([C:19]#[N:20])=[C:17]([CH3:21])[N:16]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:15](=[O:32])[NH:14]2)=[C:7]([S:9](Cl)(=[O:11])=[O:10])[CH:8]=1)#[N:2].[CH3:33][NH:34][CH3:35].C(O)C>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C@@H:13]2[C:18]([C:19]#[N:20])=[C:17]([CH3:21])[N:16]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:15](=[O:32])[NH:14]2)=[C:7]([S:9]([N:34]([CH3:35])[CH3:33])(=[O:11])=[O:10])[CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 702EthanolHCID 86664123HCID 86664123, compound

Product 1

HCID 46928898HCID 46928898, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Cyano-2-{(4S)-5-cyano-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzenesulfonyl chloride (40 mg, 83 μmol) was dissolved in THF (5 ml), a 33% strength solution of dimethylamine in ethanol (37 μl, 208 μmol; 2.5 eq.) was added at room temperature and the mixture was stirred overnight. The reaction mixture was then concentrated under reduced pressure and the residue was purified by preparative HPLC (column: Gromsil C-18, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). This gave a colorless amorphous solid (13.8 mg, 34% of theory).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (column: Gromsil C-18, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)
  3. customThis gave a colorless amorphous solid (13.8 mg, 34% of theory)

Sources & evidence

ORD record
ord-1952753f1531420b9f51f9610d88197d
Source dataset
uspto-grants-2014_04
Patent number
US08691817B2

Reaction notes

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