HCID 178437599, compound → HCID 178437600, compound

HRID 81233Notes

Reaction equation

HRID 81233 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/APCl 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-ae213edf51854376ad470f5eb3d391e6
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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