HCID 59166155, compound → HCID 59165943, compound

HRID 2188951Notes

Reaction equation

HRID 2188951 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([NH:13][C:14]([C:16]3([C:19]4[CH:29]=[CH:28][C:22]5[O:23][C:24]([F:27])([F:26])[O:25][C:21]=5[CH:20]=4)[CH2:18][CH2:17]3)=[O:15])[CH:10]=[CH:9][C:8]=2[CH3:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[H][H]>[Pd].CO>[CH:1]1([C:7]2[N:12]=[C:11]([NH:13][C:14]([C:16]3([C:19]4[CH:29]=[CH:28][C:22]5[O:23][C:24]([F:27])([F:26])[O:25][C:21]=5[CH:20]=4)[CH2:18][CH2:17]3)=[O:15])[CH:10]=[CH:9][C:8]=2[CH3:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 59166155HCID 59166155, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59165943HCID 59165943, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(6-Cyclohexenyl-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (82.4 mg, 0.200 mmol) was added to a flask containing 20 mg of 10% palladium on carbon under an atmosphere of argon. Methanol (5 mL) was added and then the reaction atmosphere was replaced with an atmosphere of hydrogen. The mixture was stirred vigorously for 16 hours. The atmosphere was then replaced with argon. The mixture was filtered, evaporated to dryness, and then purified on silica gel utilizing a gradient of 0-30% ethyl acetate in hexanes to yield N-(6-cyclohexyl-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclo-propanecarboxamide. ESI-MS m/z calc. 414.2. found; 415.1 (M+1)+ Retention time 1.78 minutes.

Workup

  1. customthe reaction atmosphere
  2. filtrationThe mixture was filtered
  3. customevaporated to dryness
  4. custompurified on silica gel utilizing a gradient of 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0fae067572344f959f7aa45ff21eae2b
Source dataset
uspto-grants-2012_12
Patent number
US08324207B2

Reaction notes

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