Cyclohexanecarboxaldehyde → HCID 22278001, compound

HRID 1064089Notes

Reaction equation

HRID 1064089 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[NH:12][NH:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:21]1([CH:27]=O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(Cl)(Cl)Cl>[CH:21]1([CH2:27][N:12]2[CH:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[C:10](=[O:20])[NH:11]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 16275CyclohexanecarboxaldehydeHCID 222779944-(3,4-Dichloro-phenyl)-5-pyridin-4-yl-pyrazolidin-3-one

Product 1

HCID 22278001HCID 22278001, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(3,4-Dichloro-phenyl)-5-pyridin-4-yl-pyrazolidin-3-one 0.30 g and 0.2 mL cyclohexanecarbaldehyde in chloroform 20 mL was added NaBH3(CN) 0.1 g at 0° C., the reaction was warmed 50° C. and stirred for 1 hour. The reaction was quenched with sat.NaHCO3 25 mL at 0° C. The reaction mixture was extracted with dichloromethane, 3×50 mL. The combined organic phase was washed with brine, dried over anhydrous Na2SO4. After purification by flash chromatography, the title compound was obtained as yellow solid 0.4 g. MS (ES+): 404 (M+H)+.

Workup

  1. customThe reaction was quenched
  2. customat 0° C
  3. extractionThe reaction mixture was extracted with dichloromethane, 3×50 mL
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-5b5724a7873a4f908b4ec667f72a705c
Source dataset
uspto-grants-2005_11
Patent number
US06967254B2

Reaction notes

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