Water → Tak-137

HRID 1405869Notes

Reaction equation

[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]([NH2:20])=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].O>CN(C)C(=O)C>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15]3=[N:20][S:24](=[O:26])(=[O:25])[CH2:23][CH2:22][N:16]3[CH:17]=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 3-(4-phenoxyphenyl)pyridin-2-amine (301 mg) in N,N-dimethylacetoamide (3 mL) was added dropwise to 2-chloroethanesulfonyl chloride (382 mg) and additional N,N-dimethylacetoamide (2 mL) was used to complete the addition of above solution. After being stirred at 60° C. for 4 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 THF (3 mL), and dried in vacuo at 60° C. to give the title compound (346.7 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-efa28ae00b3c4eb98d1cf79a00dafcf5
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916551B2

Reaction notes

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