HCID 178437599, compound → HCID 178437600, compound

HRID 1852838Notes

Reaction equation

HRID 1852838 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=2)[C:5]2[N:15]([CH2:27][C@H:28]3[CH2:33][CH2:32][C@H:31]([CH3:34])[CH2:30][CH2:29]3)[C:16]([C:18]([C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH2:19])=[N:17][C:4]=2[CH:3]=1>CCOC(C)=O.[Pt](=O)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=2)[C:5]2[N:15]([CH2:27][C@H:28]3[CH2:29][CH2:30][C@H:31]([CH3:34])[CH2:32][CH2:33]3)[C:16]([CH:18]([C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=3)[CH3:19])=[N:17][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 178437599HCID 178437599, compound

Product 1

HCID 178437600HCID 178437600, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 6-chloro-4-(5-chloropyridin-3-yl)-2-[1-(3-fluoropyridin-2-yl)ethenyl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (530 mg, 1.07 mmol) in EtOAc (12 mL) was added platinum(IV) oxide (53 mg). The reaction was placed under a H2 atmosphere and stirred for 3 h. The reaction was filtered through celite, washing with MeOH, and the filtrate was concentrated. The residue was purified by silica gel chromatography (eluting with 38-50% EtOAc/petroleum ether) to yield 6-chloro-4-(5-chloropyridin-3-yl)-2-[1-(3-fluoropyridin-2-yl)ethyl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine. MS ES/APCI calcd. for C26H26Cl2FN5 [M+H]+ 498. found 498.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel chromatography (eluting with 38-50% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-0f3edaf8639b4e6195d110d408b87856
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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