Potassium Carbonate → HCID 86660774, compound

HRID 1046870Notes

Reaction equation

HRID 1046870 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.I[CH2:26][C:27]#[N:28].[CH2:29]([O:36][C:37](=[O:69])[NH:38][C:39]1[N:68]=[C:42]2[N:43]([C:58]3[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([F:67])([F:66])[F:65])[CH:59]=3)[C:44]([CH3:57])=[C:45]([C:55]#[N:56])[C@@H:46]([C:47]3[CH:52]=[CH:51][C:50]([C:53]#[N:54])=[CH:49][CH:48]=3)[N:41]2[N:40]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[CH2:29]([O:36][C:37](=[O:69])[N:38]([C:39]1[N:68]=[C:42]2[N:43]([C:58]3[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([F:67])([F:65])[F:66])[CH:59]=3)[C:44]([CH3:57])=[C:45]([C:55]#[N:56])[C@@H:46]([C:47]3[CH:48]=[CH:49][C:50]([C:53]#[N:54])=[CH:51][CH:52]=3)[N:41]2[N:40]=1)[CH2:26][C:27]#[N:28])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 69356IodoacetonitrileHCID 70223867HCID 70223867, compound

Product 1

HCID 86660774HCID 86660774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (15.7 mg, 113 mmol, 2.1 eq.), 18-crown-6 (30 mg, 113 mmol, 2.1 eq.) and iodoacetonitrile (19 mg, 113 mmol, 2.1 eq.) were added to a solution of benzyl{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}carbamate (30 mg, 54 mmol) in DMF (2 ml). The reaction mixture was stirred at RT for 12 h and then concentrated under reduced pressure. The residue was acidified with acetic acid and then purified by preparative HPLC (Kromasil C18 column, 5 μm, 50×20 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (25 mg, 78% of theory).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by preparative HPLC (Kromasil C18 column, 5 μm, 50×20 mm; mobile phase: acetonitrile-water-0.1% TFA)
  3. customAfter lyophilization, the product was obtained as a solid (25 mg, 78% of theory)

Sources & evidence

ORD record
ord-7fb81502662343e895b15dae4ea62849
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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