Acetic Acid → N-(1-Adamantylmethyl)-5-chloro-2-formylisonicotinamide

HRID 1247607Notes

Reaction equation

HRID 1247607 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:23])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH:21]=C)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(O)(=[O:26])C>ClCCl>[C:1]12([CH2:11][NH:12][C:13](=[O:23])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH:21]=[O:26])[CH:15]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 21906707N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide

Product 1

HCID 21906741N-(1-Adamantylmethyl)-5-chloro-2-formylisonicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide (Example 29(i)) (1.70 g) was dissolved in dichloromethane (50 mL), treated with acetic acid (1 mL) and cooled to −78° C. under nitrogen. Ozone was bubbled through the resulting solution for 2 hours while maintaining the temperature. Nitrogen was subsequently bubbled through the solution for 10 minutes and dimethylsulfide (2 mL) was added. The solution was warmed to room temperature washed with sodium bicarbonate (2×10 mL) and brine (30 mL); the organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20) to afford the sub-titled compound (1.13 g).

Workup

  1. customOzone was bubbled through the resulting solution for 2 hours
  2. temperaturewhile maintaining the temperature
  3. customNitrogen was subsequently bubbled through the solution for 10 minutes
  4. additiondimethylsulfide (2 mL) was added
  5. temperatureThe solution was warmed to room temperature
  6. washwashed with sodium bicarbonate (2×10 mL) and brine (30 mL)
  7. dry with materialthe organics were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20)

Sources & evidence

ORD record
ord-01fbfe563b2c4ee481ced2672ef9c963
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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