Morpholine → HCID 46928899, compound

HRID 2361923Notes

Reaction equation

HRID 2361923 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].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>ClCCl>[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:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)(=[O:11])=[O:10])[CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86664123HCID 86664123, compound

Product 1

HCID 46928899HCID 46928899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon protective gas, 5-cyano-2-{(4S)-5-cyano-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzenesulfonyl chloride (20 mg, 42 μmol) was dissolved in absolute dichloromethane (2.5 ml), morpholine (7.3 μl, 83 μmol; 2 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 (8.6 mg, 35% 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 (8.6 mg, 35% of theory)

Sources & evidence

ORD record
ord-7dfd188dcf674e278e4893533044c41c
Source dataset
uspto-grants-2014_04
Patent number
US08691817B2

Reaction notes

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