HCID 66628495, compound → HCID 66628248, compound

HRID 2200987Notes

Reaction equation

HRID 2200987 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][CH:32]3[CH2:34][CH2:33]3)C(=O)OCC3C=CC=CC=3)[N:19]=[C:6]2[N:5]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=2)[C:4]=1[CH3:45])#[N:2]>CO.[Pd]>[C:15]([C:12]1[CH:11]=[CH:10][C:9]([C@H:8]2[N:7]3[N:17]=[C:18]([NH:20][CH2:31][CH:32]4[CH2:33][CH2:34]4)[N:19]=[C:6]3[N:5]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:43])([F:42])[F:44])[CH:36]=3)[C:4]([CH3:45])=[C:3]2[C:1]#[N:2])=[CH:14][CH:13]=1)#[N:16]

Participants

4

Reactant 1

HCID 66628495HCID 66628495, compound

Product 1

HCID 66628248HCID 66628248, 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}(cyclopropylmethyl)carbamate (20.0 mg, 33 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 1.75 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 (10.9 mg, 70% of theory).

Workup

  1. customat RT
  2. customfor 1.75 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 (10.9 mg, 70% of theory)

Sources & evidence

ORD record
ord-ca238589694b4603a62d524e36249f3e
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

Loading…