HCID 66628233, compound → HCID 66628347, compound

HRID 1046883Notes

Reaction equation

HRID 1046883 reaction equation
C(OC(=O)[N:10]([C:13]1[N:42]=[C:16]2[N:17]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=3)[C:18]([CH3:31])=[C:19]([C:29]#[N:30])[C@@H:20]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[N:15]2[N:14]=1)[CH2:11][CH3:12])C1C=CC=CC=1>CO.[Pd]>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([C@H:20]2[N:15]3[N:14]=[C:13]([NH:10][CH2:11][CH3:12])[N:42]=[C:16]3[N:17]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:41])[F:39])[CH:33]=3)[C:18]([CH3:31])=[C:19]2[C:29]#[N:30])=[CH:26][CH:25]=1)#[N:28]

Participants

4

Reactant 1

HCID 66628233HCID 66628233, compound

Product 1

HCID 66628347HCID 66628347, 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}(ethyl)carbamate (17.0 mg, 29 μmol) was dissolved in degassed methanol (2 ml). After addition of palladium on activated carbon (10%; 2 mg), the mixture was hydrogenated under a hydrogen atmosphere (˜1 atm) at RT for 1 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 (10.9 mg, 83% of theory).

Workup

  1. customat RT
  2. customfor 1 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 (10.9 mg, 83% of theory)

Sources & evidence

ORD record
ord-8a208c9bfa3b4cfb85caab43e8039c63
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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