HCID 66628239, compound → HCID 66628212, compound

HRID 1046886Notes

Reaction equation

HRID 1046886 reaction equation
C(OC(=O)[N:10]([C:15]1[N:44]=[C:18]2[N:19]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=3)[C:20]([CH3:33])=[C:21]([C:31]#[N:32])[C@@H:22]([C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[N:17]2[N:16]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1>CO.[Pd]>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([C@H:22]2[N:17]3[N:16]=[C:15]([NH:10][CH2:11][CH:12]([CH3:14])[CH3:13])[N:44]=[C:18]3[N:19]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:43])[F:41])[CH:35]=3)[C:20]([CH3:33])=[C:21]2[C:31]#[N:32])=[CH:24][CH:25]=1)#[N:30]

Participants

4

Reactant 1

HCID 66628239HCID 66628239, compound

Product 1

HCID 66628212HCID 66628212, 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}(2-methylpropyl)-carbamate (25.0 mg, 41 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 0.75 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 (13.6 mg, 70% of theory).

Workup

  1. customat RT
  2. customfor 0.75 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 (13.6 mg, 70% of theory)

Sources & evidence

ORD record
ord-8750a757bf6c4463818a9482fb14c28a
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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