Acetic Acid → HCID 66628239, compound

HRID 1046871Notes

Reaction equation

HRID 1046871 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.I[CH2:26][CH:27]([CH3:29])[CH3:28].[CH2:30]([O:37][C:38](=[O:70])[NH:39][C:40]1[N:69]=[C:43]2[N:44]([C:59]3[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:67])[F:66])[CH:60]=3)[C:45]([CH3:58])=[C:46]([C:56]#[N:57])[C@@H:47]([C:48]3[CH:53]=[CH:52][C:51]([C:54]#[N:55])=[CH:50][CH:49]=3)[N:42]2[N:41]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O)(=O)C>CN(C=O)C>[CH2:30]([O:37][C:38](=[O:70])[N:39]([C:40]1[N:69]=[C:43]2[N:44]([C:59]3[CH:64]=[CH:63][CH:62]=[C:61]([C:65]([F:68])([F:66])[F:67])[CH:60]=3)[C:45]([CH3:58])=[C:46]([C:56]#[N:57])[C@@H:47]([C:48]3[CH:49]=[CH:50][C:51]([C:54]#[N:55])=[CH:52][CH:53]=3)[N:42]2[N:41]=1)[CH2:26][CH:27]([CH3:29])[CH3:28])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 70223867HCID 70223867, compound

Product 1

HCID 66628239HCID 66628239, 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-iodo-2-methylpropane (21 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 (3 eq.) 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, 76% 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, 76% of theory)

Sources & evidence

ORD record
ord-5f149bcae7de4fa2836eedd7f345b6a2
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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