Pyridine → HCID 178437599, compound

HRID 1852837Notes

Reaction equation

HRID 1852837 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]([CH2:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([CH3:35])[CH2:31][CH2:30]3)[C:16]([C:18]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=3)(O)[CH3:19])=[N:17][C:4]=2[CH:3]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>ClCCl>[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]([CH2:28][C@H:29]3[CH2:30][CH2:31][C@H:32]([CH3:35])[CH2:33][CH2:34]3)[C:16]([C:18]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH2:19])=[N:17][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 178467408HCID 178467408, compound

Product 1

HCID 178437599HCID 178437599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (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 (Example 8.6/8.7, Step 3; 1.2 g, 2.33 mmol) and pyridine (1.88 mL, 23.3 mmol) in dichloromethane (20 mL) was added thionyl chloride (0.85 mL, 11.67 mmol) dropwise at 0° C., and the reaction was stirred at 0° C. for 1 h. The reaction was quenched with saturated NaHCO3 solution and extracted with dichloromethane (2×25 mL). The combined organic extracts were washed with water (1×25 mL) and brine (1×25 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified on a silica gel column (eluting with 40-60% EtOAc/petroleum ether) to afford 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. MS ES/APCI calcd. for C26H24Cl2FN5 [M+H]+ 496. found 496.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted with dichloromethane (2×25 mL)
  3. washThe combined organic extracts were washed with water (1×25 mL) and brine (1×25 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column (eluting with 40-60% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-241c631b5aad4ff28db4a4c752f312cb
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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