Potassium Carbonate → HCID 66628495, compound

HRID 1046872Notes

Reaction equation

HRID 1046872 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Br[CH2:26][CH:27]1[CH2:29][CH2:28]1.[C:30]([C:32]1[C@@H:37]([C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=2)[N:36]2[N:46]=[C:47]([NH:49][C:50](=[O:59])[O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[N:48]=[C:35]2[N:34]([C:60]2[CH:65]=[CH:64][CH:63]=[C:62]([C:66]([F:69])([F:68])[F:67])[CH:61]=2)[C:33]=1[CH3:70])#[N:31]>CN(C=O)C>[CH2:52]([O:51][C:50](=[O:59])[N:49]([C:47]1[N:48]=[C:35]2[N:34]([C:60]3[CH:65]=[CH:64][CH:63]=[C:62]([C:66]([F:69])([F:67])[F:68])[CH:61]=3)[C:33]([CH3:70])=[C:32]([C:30]#[N:31])[C@@H:37]([C:38]3[CH:39]=[CH:40][C:41]([C:44]#[N:45])=[CH:42][CH:43]=3)[N:36]2[N:46]=1)[CH2:26][CH:27]1[CH2:29][CH2:28]1)[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 81503BromomethylcyclopropaneHCID 70223867HCID 70223867, compound

Product 1

HCID 66628495HCID 66628495, 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 1-(bromomethyl)cyclopropane (15.3 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 (22 mg, 66% 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 (22 mg, 66% of theory)

Sources & evidence

ORD record
ord-12acc984bcff45fa90174172695e8605
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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