Lithium Chloride → 1-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-cyclobutanecarboxylic acid hyrdochloride salt

HRID 902757Notes

Reaction equation

HRID 902757 reaction equation
C[O:2][C:3]([C:5]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[C:36]=3[Cl:45])[CH2:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:10]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[Li+].[Cl-]>CN(C=O)C>[ClH:45].[Cl:45][C:36]1[C:37]([C:41]([F:42])([F:43])[F:44])=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][N:19]([CH2:20][CH:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:18][CH2:17][CH2:16][O:15][C:11]1[CH:10]=[C:9]([C:5]2([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][CH2:8]2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 69253567HCID 69253567, compound

Product 1

HCID 692533271-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-cyclobutanecarboxylic acid hyrdochloride salt

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-cyclobutanecarboxylic acid methyl ester (40 mg, 0.06 mmol) in DMF (9 ml) was treated with LiCl (20 mg, 0.46 mmol). The resulting reaction mixture was heated to reflux overnight and concentrated under vacuum. The crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: acetonitrile B: water, A: 60 to 100% during 10 min, W detection at 254 nm) to give the title compound, the free amine as an oil (20 mg, 50%). MS m/e 622.2 (M+H)+. To a solution of the free amine in diethyl ether was added HCl in diethyl ether (1.0M) to precipitate the amine salt. The suspension was filtered and dried to give the title compound as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

Sources & evidence

ORD record
ord-f4749ebac9b348e7a68838fda7156d5d
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

Loading…