Methanesulfonamide → HCID 135600031, compound

HRID 1175825Notes

Reaction equation

HRID 1175825 reaction equation
[NH2:1][C:2]1[N:3]([C:16]2[C:17]([CH3:27])=[C:18]([CH:24]=[CH:25][CH:26]=2)[O:19][CH2:20][C:21](O)=[O:22])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7](=[O:15])[C:6]=12.[CH3:28][S:29]([NH2:32])(=[O:31])=[O:30]>CN(C)C1C=CN=CC=1.CN(C)C=O>[NH2:1][C:2]1[N:3]([C:16]2[C:17]([CH3:27])=[C:18]([CH:24]=[CH:25][CH:26]=2)[O:19][CH2:20][C:21]([NH:32][S:29]([CH3:28])(=[O:31])=[O:30])=[O:22])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7](=[O:15])[C:6]=12

Participants

5

Reactant 2

HCID 72879MethanesulfonamideHCID 135599852HCID 135599852, compound

Product 1

HCID 135600031HCID 135600031, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of [3-(3-amino-4-oxo-4,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)-2-methylphenoxy]acetic acid (64 mg), methanesulfonamide (50 mg), 4-(dimethylamino)pyridine (25 mg), (3-dimethylaminopyropyl)ethylcarbodiimide hydrochloride (40 mg) and N,N-dimethylformamide (6 ml) was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure. To the residue was added water, and then pH of the residue was adjusted to about 2 by adding a 1N hydrochloric acid. The precipitated solid was collected by filtration, washed with water, and dried to obtain the target compound (29 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added water
  3. additionby adding a 1N hydrochloric acid
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-622661fe7ac64d688e99e90e266c98d9
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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