5-(1-(t-butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine → 5-(1-(t-butoxycarbonyl)piperidin-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

HRID 897407Notes

Reaction equation

HRID 897407 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:19]3[CH:20]=[N:21][N:22]=[C:18]3[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)=[C:16]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:39][C@H:40]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH3:41])[CH:34]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:19]3[CH:20]=[N:21][N:22]=[C:18]3[C:17]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:32])[F:30])[CH:24]=3)=[C:16]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:39][C@H:40]([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH3:41])[CH:34]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 208169045-(1-(t-butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Product 1

HCID 208169055-(1-(t-butoxycarbonyl)piperidin-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

5-(1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-(1(S)-phenylethyl)amino-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine (0.12 g, 0.2 mmol) and platinum oxide (0.03 g, 0.13 mmol) were combined in ethanol (5 ml) and maintained at room temperature under an atmosphere of hydrogen for 18 hours. The catalyst was removed by filtration and the filtrate was concentrated to a syrup. The residue was purified by column chromatography on silica gel (30% ethyl acetate in hexane) to give the product as a syrup; MS m/z (M+H)+ 644.5; C35H36F3N7O2 require 643.3.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to a syrup
  3. customThe residue was purified by column chromatography on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5470fb357d0c45a1adf99e2e09afbc32
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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