Pyridine → n-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-acetamide hydrochloride salt

HRID 902633Notes

Reaction equation

HRID 902633 reaction equation
[Cl:1][C:2]1[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][N:5]([CH2:17][CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=1.N1C=CC=CC=1.[C:45](Cl)(=[O:47])[CH3:46]>ClCCl>[ClH:1].[Cl:1][C:2]1[C:34]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:32]=[CH:31][C:3]=1[CH2:4][N:5]([CH2:17][CH:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([NH:16][C:45](=[O:47])[CH3:46])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 101287483-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethylamino]-propoxy}-phenylamine

Product 1

HCID 69253155n-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-acetamide hydrochloride saltYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethylamino]-propoxy}-phenylamine (80.0 mg, 0.15 mmol) dissolved in anhydrous dichloromethane (1 mL) was added pyridine (18 uL, 0.22 mmol) and acetyl chloride (12.7 uL, 0.18 mmol) at room temperature. The reaction was maintained for 60 hours after which the solvent was removed under reduced pressure. The residue was purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: acetonitrile B: water, A: 5 to 95% over 15 min, UV detection at 214 nm and 254 nm) and the resulting residue after solvent removal was treated with aqueous 6N HCl (0.5 mL) and acetonitrile (2 mL). The solvent was removed under reduced pressure to give 41.4 mg (0.07 mmol, 47%) of the title compound as a colorless oil. MS (ESI) 581.0

Workup

  1. temperatureThe reaction was maintained for 60 hours after which the solvent
  2. customwas removed under reduced pressure
  3. customThe residue was purified by preparative HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min
  4. customUV detection at 214 nm and 254 nm) and the resulting residue after solvent removal
  5. additionwas treated with aqueous 6N HCl (0.5 mL) and acetonitrile (2 mL)
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-638d5d2ea6de490ea9646b2f9de8b2e8
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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