Ro 48-8071 → HCID 18434102, compound

HRID 1636751Notes

Reaction equation

HRID 1636751 reaction equation
[CH2:1]([N:4]([CH3:28])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[O:19])=[C:14](F)[CH:13]=1)[CH:2]=[CH2:3].[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH2:1]([N:4]([CH3:28])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[O:19])=[C:14]([NH:36][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([O:30][CH3:29])=[CH:32][CH:33]=2)[CH:13]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 1949Ro 48-8071HCID 11430Potassium CarbonateHCID 754524-Methoxybenzylamine

Product 1

HCID 18434102HCID 18434102, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Analogously to Example 33, 17.55 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl]-(4-bromo-phenyl)-methanone are boiled under reflux for 23 hrs. with 50.7 ml of 4-methoxy-benzylamine and 6.5 g of potassium carbonate in 600 ml of toluene. After filtration, evaporation and purification over silica gel with methylene chloride/methanol (2.5% to 10%) there are obtained 17.43 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-(4-methoxy-benzylamino)-phenyl]-(4-bromo-phenyl)-methanone. A solution of this material in 200 ml of trifluoroacetic acid is stirred at room temperature for 45 hrs., evaporated and the residue is converted into the free base with methylene chloride/saturated sodium bicarbonate solution. After purification over silica gel with methylene chloride/methanol (9:1) there are obtained 13.23 g of [2-amino-4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl]-(4-bromo-phenyl)-methanone.

Workup

  1. temperatureunder reflux for 23 hrs
  2. filtrationAfter filtration, evaporation and purification over silica gel with methylene chloride/methanol (2.5% to 10%) there

Sources & evidence

ORD record
ord-b0b6f8706cd64107a5c15717caea178e
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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