Triethylamine → HCID 46929086, compound

HRID 2361931Notes

Reaction equation

HRID 2361931 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])[N:14]2[CH3:33])=[C:7]([S:9](Cl)(=[O:11])=[O:10])[CH:8]=1)#[N:2].[NH2:34][CH2:35][CH2:36][CH2:37][OH:38].C(N(CC)CC)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])[N:14]2[CH3:33])=[C:7]([S:9]([NH:34][CH2:35][CH2:36][CH2:37][OH:38])(=[O:11])=[O:10])[CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 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 46929086HCID 46929086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of argon protective gas, 5-cyano-2-{(4S)-5-cyano-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzenesulfonyl chloride (25 mg, 51 μmol) was dissolved in absolute THF (1.5 ml), 3-aminopropanol (11 μl, 152 μmol; 3 eq.) and triethylamine (5.1 mg, 51 μmol; 1 eq.) were 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: Kromasil C-18, 5 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). This gave a colorless amorphous solid (18 mg, 67% of theory).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (column: Kromasil C-18, 5 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)
  3. customThis gave a colorless amorphous solid (18 mg, 67% of theory)

Sources & evidence

ORD record
ord-414965e6377544029ec70c3d610e45a8
Source dataset
uspto-grants-2014_04
Patent number
US08691817B2

Reaction notes

Loading…