2-Dimethylaminopyridine → HCID 18434212, compound

HRID 1636752Notes

Reaction equation

HRID 1636752 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:17][CH:18]=[CH2:19])[CH3:16])[CH:5]=[CH:4][C:3]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)=[O:21].[CH3:29][S:30](Cl)(=[O:32])=[O:31].CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH2:17]([N:15]([CH3:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([C:20](=[O:21])[C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)=[C:2]([NH:1][S:30]([CH3:29])(=[O:32])=[O:31])[CH:7]=1)[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 10873957HCID 10873957, compound

Product 1

HCID 18434212HCID 18434212, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.9 g of [2-amino-4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl]-(4-bromo-phenyl)-methanone (Ex. 36) is treated in 20 ml of methylene chloride at 0° C. with 0.17 ml of methanesulphonyl chloride in 0.8 ml of methylene chloride and with 24.4 mg of dimethylaminopyridine. The reaction mixture is left to warm to room temperature overnight and concentrated and the residue is taken up in methylene chloride/saturated sodium bicarbonate solution. The organic phase is dried and concentrated. Purification over silica gel with methylene chloride/methanol (95:5) as the eluent gives 0.57 g of N-[5-[6-(allyl-methyl-amino)-hexyloxy]-2-(4-bromo-benzoyl)-phenyl]-methanesulphonamide which is converted into the fumarate, MS: m/e 523 (M+H+, 1Br).

Workup

  1. waitThe reaction mixture is left
  2. concentrationconcentrated
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customPurification over silica gel with methylene chloride/methanol (95:5) as the eluent

Sources & evidence

ORD record
ord-0803986347b941428d5f53d4df35f09b
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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