HCID 66627834, compound → HCID 66628540, compound

HRID 2200985Notes

Reaction equation

HRID 2200985 reaction equation
[C:1]([C:3]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:7]2[N:17]=[C:18]([N:20]([CH2:31][CH2:32][CH3:33])C(=O)OCC3C=CC=CC=3)[N:19]=[C:6]2[N:5]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=2)[C:4]=1[CH3:44])#[N:2]>CO.[Pd]>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([C@H:8]2[N:7]3[N:17]=[C:18]([NH:20][CH2:31][CH2:32][CH3:33])[N:19]=[C:6]3[N:5]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:42])([F:43])[F:41])[CH:35]=3)[C:4]([CH3:44])=[C:3]2[C:1]#[N:2])=[CH:10][CH:11]=1)#[N:16]

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-56d5f2b9008a4a559d1d50f4e435aa50
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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