Dichloromethane → N-(1-Adamantylmethyl)-5-chloro-2-(3-oxopropyl)isonicotinamide

HRID 1247605Notes

Reaction equation

HRID 1247605 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH2:21][CH2:22][CH2:23][OH:24])[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.ClCCl.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)C>[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH2:21][CH2:22][CH:23]=[O:24])[CH:15]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 21906688N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxypropyl)isonicotinamide

Product 1

HCID 21906722N-(1-Adamantylmethyl)-5-chloro-2-(3-oxopropyl)isonicotinamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of N-(1-adamantylmethyl)-5-chloro-2-(3-hydroxypropyl)isonicotinamide (0.12 g, 0.33 mmol) (Example 14(ii)) in dry dichloromethane (10 mL) Dess-Martin periodinane (0.14 g, 0.33 mmol) was added. The resulting mixture was stirred at room temperature for 4 hours. The reaction was treated with diethyl ether (20 mL) and a saturated sodium bicarbonate solution containing sodium thiosulfate (0.37 g, in 4 mL). The mixture was stirred for 10 minutes and the organics separated; washed with brine (10 mL); dried over anhydrous magnesium sulfate; filtered; treated with acetic acid (0.30 mL) and concentrated. MS: APCI(+ve) 361, 363 (M+1).

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. washwashed with brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. additiontreated with acetic acid (0.30 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8bba5c38fdd4e23a85948c3e6a25e68
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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