Thioanisole → HCID 86692459, compound

HRID 1748509Notes

Reaction equation

HRID 1748509 reaction equation
C1(SC)C=CC=CC=1.COC1C=CC(C[NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3([C:29]#[N:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[N:21][CH:22]=2)=CC=1.[OH-].[Na+]>>[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2([C:29]#[N:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[N:21][CH:22]=1

Participants

4

Reactant 3

HCID 7520ThioanisoleHCID 14798Sodium HydroxideHCID 86692458HCID 86692458, compound

Product 1

HCID 86692459HCID 86692459, compoundYield 91%

Conditions

Temperature
40 °C

Procedure

Trifluoroacetc acid (4 ml) and thioanisole (1.2 ml) were added to 1-{5-[(4-methoxybenzyl)amino]pyridin-2-yl}cyclohexanecarbonitrile (632 mg) and stirred at 40° C. for 1.5 hours. An aqueous solution of sodium hydroxide was added and the mixture was adjusted to pH 10. The solution was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give the titled compound (360 mg) as a solid.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b97350d2c046473b940c263e60015309
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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