Ro 48-8071 → HCID 18434102, compound

HRID 342225Notes

Reaction equation

HRID 342225 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

17.55 g of [4-[6-(allyl-methyl-amino)-hexyloxy]-2-fluoro-phenyl]-(4-bromo-phenyl)-methanone are boiled under reflux with 50.7 ml of 4-methoxybenzylamine and 6.5 g of potassium carbonate in 600 ml of toluene for 23 hrs. 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-benzyl)amino]-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 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, m.p. of the fumarate 78° C.(decomposition).

Workup

  1. filtrationAfter filtration, evaporation and purification over silica gel with methylene chloride/methanol (2.5% to 10%) there

Sources & evidence

ORD record
ord-8082361ef1c548249d3ae5d4f12322f8
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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