Benzenesulfonyl chloride → HCID 57749183, compound

HRID 1874559Notes

Reaction equation

HRID 1874559 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[C:24]1([S:30]([NH:1][C:2]2[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=2)[O:5][C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])[N:14]=3)[CH:11]=2)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 57749361N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749183HCID 57749183, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (18.6 mg, 0.060 mmol), benzenesulfonyl chloride (12.8 μL, 0.100 mmol), tetrahydrofuran (3 mL) and aqueous sodium hydrogen carbonate solution (2 mL) was stirred at room temperature for 4 hr. The reaction mixture was extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by preparative HPLC to give the title compound (10.9 mg, 41%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c931fa126cc746ad87bbf2d78e50fd08
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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