HCID 178418573, compound → HCID 178467408, compound

HRID 81229Notes

Reaction equation

HRID 81229 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)=[O:19])=[N:17][C:4]=2[CH:3]=1.[CH3:35][Mg]Br>C1COCC1>[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)([OH:19])[CH3:35])=[N:17][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 178418573HCID 178418573, compoundHCID 178461202HCID 178461202, compound

Product 1

HCID 178467408HCID 178467408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-2-yl}(3-fluoropyridin-2-yl)methanone (618 mg, 1.24 mmol) in THF (10 mL) was added methyl magnesium bromide (3 M in diethyl ether, 0.82 mL, 2.46 mmol) at −78° C., and the reaction mixture was stirred for 2 hours. The reaction mixture was quenched with aqueous saturated NH4Cl solution (40 mL) and extracted with ethyl acetate (2×35 mL). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated. Purification of the residue on a silica gel column (0 to 100% EtOAc/hexanes) afforded (1RS)-1-{6-chloro-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-2-yl}-1-(3-fluoropyridin-2-yl)ethanol. MS APCl calcd. for C26H26Cl2FN5O [M+H]+ 514. found 514.

Workup

  1. customThe reaction mixture was quenched with aqueous saturated NH4Cl solution (40 mL)
  2. extractionextracted with ethyl acetate (2×35 mL)
  3. washThe combined organic extracts were washed with brine (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue on a silica gel column (0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-33530c1afd494007b77fb31d251dba05
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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