Ammonia → HCID 66734869, compound

HRID 2361929Notes

Reaction equation

HRID 2361929 reaction equation
N.O1CCOCC1.C([N:10](CC)CC)C.[C:15]([C:17]1[CH:18]=[CH:19][C:20]([C@@H:27]2[C:32]([C:33]#[N:34])=[C:31]([CH3:35])[N:30]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=3)[C:29](=[O:46])[N:28]2[CH3:47])=[C:21]([S:23](Cl)(=[O:25])=[O:24])[CH:22]=1)#[N:16]>>[C:15]([C:17]1[CH:18]=[CH:19][C:20]([C@@H:27]2[C:32]([C:33]#[N:34])=[C:31]([CH3:35])[N:30]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=3)[C:29](=[O:46])[N:28]2[CH3:47])=[C:21]([S:23]([NH2:10])(=[O:25])=[O:24])[CH:22]=1)#[N:16]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 866507215-Cyano-2-{(4S)-5-cyano-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzenesulfonyl chloride

Product 1

HCID 66734869HCID 66734869, compound

Procedure

Under an atmosphere of argon protective gas, a 0.5 M solution of ammonia in dioxane (4000 μl, 2021 μmol; 10 eq.) and triethylamine (20.4 mg, 202 μmol; 1 eq.) were added to 5-cyano-2-{(4S)-5-cyano-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzenesulfonyl chloride (100 mg, 202 μmol) at room temperature, and the mixture was stirred for 3 h. The reaction mixture was then concentrated under reduced pressure and the residue was purified by preparative HPLC (column: Gromsil C-18; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). This gave a colorless amorphous solid (56 mg, 58% 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; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)
  3. customThis gave a colorless amorphous solid (56 mg, 58% of theory)

Sources & evidence

ORD record
ord-ff0a9cd1f0a64d4390ac630208a2f23b
Source dataset
uspto-grants-2014_04
Patent number
US08691817B2

Reaction notes

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