HCID 46841341, compound → HCID 46841208, compound

HRID 2200988Notes

Reaction equation

HRID 2200988 reaction equation
C(OC([N:11]([C:20]1[N:49]=[C:23]2[N:24]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=3)[C:25]([CH3:38])=[C:26]([C:36]#[N:37])[C@@H:27]([C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=3)[N:22]2[N:21]=1)[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O)C1C=CC=CC=1>CO.[Pd]>[C:36]([C:26]1[C@@H:27]([C:28]2[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=2)[N:22]2[N:21]=[C:20]([NH:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[N:49]=[C:23]2[N:24]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:46])([F:47])[F:48])[CH:40]=2)[C:25]=1[CH3:38])#[N:37]

Participants

4

Reactant 1

HCID 46841341HCID 46841341, compound

Product 1

HCID 46841208HCID 46841208, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under an atmosphere of argon protective gas, tert-butyl N-[(benzyloxy)carbonyl]-N-{(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}glycinate (23.0 mg, 34 μmol) was dissolved in degassed methanol (2.3 ml). After addition of palladium on activated carbon (10%-ig; 15.2 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 (21.2 mg, quant.).

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 (21.2 mg, quant.)

Sources & evidence

ORD record
ord-a22f1595161745339eca90d3122905db
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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