Ammonia → HCID 46928896, compound

HRID 2361920Notes

Reaction equation

HRID 2361920 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])[NH:28]2)=[C:21]([S:23](Cl)(=[O:25])=[O:24])[CH:22]=1)#[N:16]>C(#N)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])[NH:28]2)=[C:21]([S:23]([NH2:10])(=[O:25])=[O:24])[CH:22]=1)#[N:16]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 86664123HCID 86664123, compound

Product 1

HCID 46928896HCID 46928896, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At room temperature, a 0.5 M solution of ammonia in dioxane (25.79 ml, 12.9 mmol; 10 eq.) and triethylamine (130 mg, 1.3 mmol; 1 eq.) were added to 5-cyano-2-{(4S)-5-cyano-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzenesulfonyl chloride (3.10 g, content 20%, 1.29 mmol), and the mixture was stirred overnight. The reaction mixture was then concentrated under reduced pressure, water/acetonitrile (˜10:1) was added to the residue and the solution was lyophilized. The substance obtained was dissolved in acetonitrile and then purified by preparative HPLC (column: Waters Sunfire C18, 5 μm; column dimensions: 250 mm×20 mm; detection: 240 nm; temperature: 28° C.; flow rate: 25 ml/min; injection volume: 500 μl; mobile phase: acetonitrile/0.2% trifluoroacetic acid 45:55). The title compound was obtained as a solid (0.155 g, 26% of theory).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure, water/acetonitrile (˜10:1)
  2. additionwas added to the residue
  3. customThe substance obtained
  4. custompurified by preparative HPLC (column: Waters Sunfire C18, 5 μm; column dimensions: 250 mm×20 mm; detection: 240 nm; temperature: 28° C.; flow rate: 25 ml/min; injection volume: 500 μl; mobile phase: acetonitrile/0.2% trifluoroacetic acid 45:55)

Sources & evidence

ORD record
ord-263a15e6a04f46969b1ac5a70c445a7c
Source dataset
uspto-grants-2014_04
Patent number
US08691817B2

Reaction notes

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