HCID 66627834, compound → HCID 66628540, compound

HRID 1046885Notes

Reaction equation

HRID 1046885 reaction equation
C(OC(=O)[N:10]([C:14]1[N:43]=[C:17]2[N:18]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=3)[C:19]([CH3:32])=[C:20]([C:30]#[N:31])[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)[N:16]2[N:15]=1)[CH2:11][CH2:12][CH3:13])C1C=CC=CC=1>CO.[Pd]>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([C@H:21]2[N:16]3[N:15]=[C:14]([NH:10][CH2:11][CH2:12][CH3:13])[N:43]=[C:17]3[N:18]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:41])([F:42])[F:40])[CH:34]=3)[C:19]([CH3:32])=[C:20]2[C:30]#[N:31])=[CH:23][CH:24]=1)#[N:29]

Participants

4

Reactant 1

HCID 66627834HCID 66627834, compound

Product 1

HCID 66628540HCID 66628540, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under an atmosphere of argon protective gas, 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}(propyl)carbamate (17.0 mg, 28 μmol) was dissolved in degassed methanol (5 ml). After addition of palladium on activated carbon (10%; 5 mg), the mixture was hydrogenated under a hydrogen atmosphere (˜1 atm) at RT for 0.5 h. The reaction mixture was then filtered, the filtrate was concentrated under reduced pressure and the residue was purified by preparative HPLC (Kromasil C18 column, 50×20 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (10.7 mg, 81% of theory).

Workup

  1. customat RT
  2. customfor 0.5 h
  3. filtrationThe reaction mixture was then filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by preparative HPLC (Kromasil C18 column, 50×20 mm; mobile phase: acetonitrile-water-0.1% TFA)
  6. customAfter lyophilization, the product was obtained as a solid (10.7 mg, 81% of theory)

Sources & evidence

ORD record
ord-dbfa9720db8f470d9b7b8839520a69a9
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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