Potassium Carbonate → HCID 46841341, compound

HRID 1046873Notes

Reaction equation

HRID 1046873 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH2:16]([O:23][C:24](=[O:56])[NH:25][C:26]1[N:55]=[C:29]2[N:30]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=3)[C:31]([CH3:44])=[C:32]([C:42]#[N:43])[C@@H:33]([C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=3)[N:28]2[N:27]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:23][C:24]([N:25]([C:26]1[N:55]=[C:29]2[N:30]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:52])[F:53])[CH:46]=3)[C:31]([CH3:44])=[C:32]([C:42]#[N:43])[C@@H:33]([C:34]3[CH:35]=[CH:36][C:37]([C:40]#[N:41])=[CH:38][CH:39]=3)[N:28]2[N:27]=1)[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:56])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 70223867HCID 70223867, compound

Product 1

HCID 46841341HCID 46841341, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (8.0 mg, 58 μmol, 1.6 eq.) and tert-butyl bromoacetate (11.2 mg, 58 μmol, 1.6 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 (20 mg, 36 μmol) in dry DMF (5 ml). The reaction mixture was stirred at RT for 12 h and then concentrated under reduced pressure, and the residue 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, 76% of theory).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue purified 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, 76% of theory)

Sources & evidence

ORD record
ord-8b7a709c1d5f4109a2e39aeadd771379
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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