Water → 2-(4-Fluorophenyl)-4-(3-methanesulfonylaminopropyl)-3-(pyridin-4-yl)-1H-pyrrole

HRID 1245007Notes

Reaction equation

HRID 1245007 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=O)=[O:3].[NH2:10][CH2:11][CH2:12][CH2:13][C:14]1[C:15]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[NH:17][CH:18]=1.O>N1C=CC=CC=1>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[NH:17][CH:18]=[C:14]([CH2:13][CH2:12][CH2:11][NH:10][S:2]([CH3:1])(=[O:5])=[O:3])[C:15]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 81560Methanesulfonic anhydrideHCID 98792264-(3-Aminopropyl)-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole

Product 1

HCID 219227222-(4-Fluorophenyl)-4-(3-methanesulfonylaminopropyl)-3-(pyridin-4-yl)-1H-pyrroleYield 57%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

188 mg (1.08 mmol) of methanesulfonic anhydride were added to a solution of 290 mg (0.982 mmol) of 4-(3-aminopropyl)-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole (prepared as described in Example 1 above) in 5 ml of pyridine and the resulting mixture was allowed to stand overnight. At the end of this time, water was added to the reaction mixture, giving a precipitate which was collected by filtration and washed with ethyl acetate to give 208 mg (yield 57%) of the title compound as a pale brown powder.

Workup

  1. customgiving a precipitate which
  2. filtrationwas collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-38e0a61580bc4d5f87127dcdb2c7b7e7
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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