Potassium Carbonate → HCID 46841341, compound

HRID 2200973Notes

Reaction equation

HRID 2200973 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].[C:16]([C:18]1[C@@H:23]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[N:22]2[N:32]=[C:33]([NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:34]=[C:21]2[N:20]([C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([F:55])([F:54])[F:53])[CH:47]=2)[C:19]=1[CH3:56])#[N:17]>CN(C=O)C>[CH2:38]([O:37][C:36]([N:35]([C:33]1[N:34]=[C:21]2[N:20]([C:46]3[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([F:55])([F:53])[F:54])[CH:47]=3)[C:19]([CH3:56])=[C:18]([C:16]#[N:17])[C@@H:23]([C:24]3[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=3)[N:22]2[N:32]=1)[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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-062964b14ad449d0a22f6e2bf5ae097c
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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