Water → HCID 66750016, compound

HRID 1747934Notes

Reaction equation

HRID 1747934 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][CH:17]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].O>C1COCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[C:13]4=[N:18][S:24](=[O:26])(=[O:25])[CH2:23][CH2:22][N:14]4[CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 66748349HCID 66748349, compound

Product 1

HCID 66750016HCID 66750016, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(4-(pyrrolidin-1-yl)phenyl)pyridin-2-amine (17.0 mg) in THF (dry) (5 mL) was added to a mixture of NaH (60%, 14.2 mg) and 2-chloroethanesulfonyl chloride (34.7 mg) in THF (dry) (5.00 mL) at room temperature. The mixture was stirred at 50° C. for 1 hr. Water and NH silica gel were added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) to give the title compound (14.8 mg) as a pale yellow solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)

Sources & evidence

ORD record
ord-719533b1b042435fb4b029724c41f44c
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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