Methanesulfonyl chloride → HCID 59656646, compound

HRID 2054917Notes

Reaction equation

HRID 2054917 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:12][C:11]([CH2:21][CH2:22][NH2:23])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1.O>[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[CH:12][C:11]([CH2:21][CH2:22][NH:23][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:10][C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11450439HCID 11450439, compound

Product 1

HCID 59656646HCID 59656646, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-amino-6-(2-amino-ethyl)-4-cyclopentylmethoxy-benzo[b]thiophene-2-carboxylic acid amide (11) (HCl salt form, 0.100 g, 0.270 mmol) in pyridine (1 mL) at 0° C. was added methanesulfonyl chloride (0.08 mL, 1 mmol). It was allowed to warm to room temperature and stirred overnight. It was diluted with water, extracted with dichloromethane, washed with brine, dried with sodium sulfate, and concentrated. The residue was purified by preparatory thin layer chromatography to afford the title compound (0.021 g, 19%).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparatory thin layer chromatography

Sources & evidence

ORD record
ord-12e8d086c62c418eb3e74f8304313aaa
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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