HCID 86660774, compound → HCID 86660773, compound

HRID 1046884Notes

Reaction equation

HRID 1046884 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][C:12]#[N:13])C1C=CC=CC=1>CO.[Pd]>[C:12]([CH2:11][NH: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:41])([F:40])[F:42])[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)#[N:13]

Participants

4

Reactant 1

HCID 86660774HCID 86660774, compound

Product 1

HCID 86660773HCID 86660773, 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}(cyanomethyl)-carbamate (10.0 mg, 17 μmol) was dissolved in degassed methanol (3 ml). After addition of palladium on activated carbon (10%; 2 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 (7.4 mg, 96% 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 (7.4 mg, 96% of theory)

Sources & evidence

ORD record
ord-4d80b39ddc2a40518b047bfb0b414321
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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