Water → 9-[4-(Cyclohexyloxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1748072Notes

Reaction equation

Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[CH:8]1([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([NH2:27])=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.O>CN(C)C(=O)C>[CH:8]1([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]4=[N:27][S:4](=[O:6])(=[O:5])[CH2:3][CH2:2][N:23]4[CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-chloroethanesulfonyl chloride (381 mg) in N,N-dimethylacetoamide (2 mL) was added dropwise to a suspension of 3-[4-(cyclohexyloxy)phenyl]pyridin-2-amine (301 mg) in N,N-dimethylacetoamide (2 mL) and additional N,N-dimethylacetoamide (1 mL) was used to complete the addition of above solution. After being stirred at 60° C. for 3 hr, the mixture was cooled to room temperature. Water (10 mL) was added dropwise to the reaction mixture and the whole was stirred at room temperature for 0.5 hr. The precipitate was collected by filtration, washed with water (10 mL) and diisopropyl ether (3 mL), and dried in vacuo at 60° C. to give the title compound (342 mg) as an off-white powder.

Workup

additionthe addition of above solution
temperaturethe mixture was cooled to room temperature
stirringthe whole was stirred at room temperature for 0.5 hr
filtrationThe precipitate was collected by filtration
washwashed with water (10 mL) and diisopropyl ether (3 mL)
customdried in vacuo at 60° C.

Sources & evidence

ORD record: ord-ab5820484a0946f2be09326f63cfa206
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150591B2

Reaction notes

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