2,2-Dimethyl-n-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide → 6-Thiomorpholin-4-yl-4-o-tolyl-pyridin-3-ylamine

HRID 22645Notes

Reaction equation

CC(C)(C)C([NH:5][C:6]1[CH:7]=[N:8][C:9]([N:19]2[CH2:24][CH2:23][S:22][CH2:21][CH2:20]2)=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])=O>Cl>[N:19]1([C:9]2[N:8]=[CH:7][C:6]([NH2:5])=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH:10]=2)[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 3.45 g (9.3 mmol) 2,2-dimethyl-N-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide in 95 ml 3 N hydrochloric acid solution was heated under argon at 110° C. overnight. The reaction mixture was cooled to room temperature, washed with two 100-ml portions of diethyl ether and filtered over celite. The filtrate was diluted with 20 ml water and was adjusted to pH 11 by addition of 28% sodium hydroxide solution under ice cooling. The product was extracted with three 100-ml portions of dichloromethane. The combined organic layers were washed with 50 ml brine, dried (sodium sulfate) and evaporated to give 2.53 g (95%) of the title compound as a brown solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with two 100-ml portions of diethyl ether
filtrationfiltered over celite
additionThe filtrate was diluted with 20 ml water
additionwas adjusted to pH 11 by addition of 28% sodium hydroxide solution under ice cooling
extractionThe product was extracted with three 100-ml portions of dichloromethane
washThe combined organic layers were washed with 50 ml brine
dry with materialdried (sodium sulfate)
customevaporated

Sources & evidence

ORD record: ord-17cd5659dfd049aa869e2dddb349de12
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849624B2

Reaction notes

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