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

HRID 1748070Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-chloroethanesulfonyl chloride (208.2 mg) in N,N-dimethylacetoamide (2 mL) was added dropwise to a suspension of 3-(3-fluorobiphenyl-4-yl)pyridin-2-amine (149.5 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 h, 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 THF (3 mL), and dried in vacuo at 60° C. to give the title compound (143 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 THF (3 mL)
customdried in vacuo at 60° C.

Sources & evidence

ORD record: ord-868672fc811847f98827a2249e51ab6d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150591B2

Reaction notes

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