Potassium Carbonate → HCID 86660774, compound

HRID 2200970Notes

Reaction equation

HRID 2200970 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.I[CH2:26][C:27]#[N:28].[C:29]([C:31]1[C@@H:36]([C:37]2[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][CH:38]=2)[N:35]2[N:45]=[C:46]([NH:48][C:49](=[O:58])[O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[N:47]=[C:34]2[N:33]([C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:67])[F:66])[CH:60]=2)[C:32]=1[CH3:69])#[N:30]>CN(C=O)C>[C:29]([C:31]1[C@@H:36]([C:37]2[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][CH:38]=2)[N:35]2[N:45]=[C:46]([N:48]([CH2:26][C:27]#[N:28])[C:49](=[O:58])[O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[N:47]=[C:34]2[N:33]([C:59]2[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:67])[F:66])[CH:60]=2)[C:32]=1[CH3:69])#[N:30]

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 μmol, 2.1 eq.), 18-crown-6 (30 mg, 113 μmol, 2.1 eq.) and iodoacetonitrile (19 mg, 113 μmol, 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 μmol) 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-485d6c57414b402fb813673541cb06b5
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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