2,4-Difluorobenzylamine → 2-adamantan-1-yl-N-[2-(2,4-difluoro-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl]-acetamide

HRID 749218Notes

Reaction equation

HRID 749218 reaction equation
[C:1]12([CH2:11][C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH2:17][CH2:18][O:19][C:20]4=O)=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[F:26][C:27]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>>[C:1]12([CH2:11][C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH2:17][CH2:18][N:30]([CH2:29][C:28]3[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:27]=3[F:26])[C:20]4=[O:19])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

3

Reactant 2

HCID 27332442,4-DifluorobenzylamineHCID 597520312-adamantan-1-yl-N-(1-oxo-isochroman-5-yl)-acetamide

Product 1

HCID 250633312-adamantan-1-yl-N-[2-(2,4-difluoro-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl]-acetamideYield 36.5%

Conditions

Temperature
160 °C

Procedure

A mixture of 2-adamantan-1-yl-N-(1-oxo-isochroman-5-yl)-acetamide (39 mg, 0.115 mmol) and 2,4-difluorobenzylamine (99 mg, 0.689 mmol) was heated at 160° C. for 40 h. The reaction vessel was cooled to room temperature and the solvents removed under reduced pressure. The crude product was purified by prep. HPLC to afford 2-adamantan-1-yl-N-[2-(2,4-difluoro-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-5-yl]-acetamide (19.2 mg, 0.042 mmol, 36%) as a white solid.

Workup

  1. temperatureThe reaction vessel was cooled to room temperature
  2. customthe solvents removed under reduced pressure
  3. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-0be5dc4c6a3e48d3a136c45357863bb7
Source dataset
uspto-grants-2008_07
Patent number
US07402596B2

Reaction notes

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