4-Fluorobenzylamine → 2-adamantan-1-yl-N-[2-(4-fluoro-benzyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-acetamide

HRID 749216Notes

Reaction equation

HRID 749216 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[CH:17]=[CH: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]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>>[C:1]12([CH2:11][C:12]([NH:14][C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH:17]=[CH:18][N:32]([CH2:31][C:30]3[CH:33]=[CH:34][C:27]([F:26])=[CH:28][CH:29]=3)[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 673264-FluorobenzylamineHCID 597520152-adamantan-1-yl-N-(1-oxo-1H-isochromen-5-yl)-acetamide

Product 1

HCID 250637982-adamantan-1-yl-N-[2-(4-fluoro-benzyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-acetamideYield 75.3%

Conditions

Temperature
145 °C

Procedure

A mixture of 2-adamantan-1-yl-N-(1-oxo-1H-isochromen-5-yl)-acetamide (0.3 g, 0.89 mmol) and 4-fluorobenzylamine 0.668 g (5.33 mmol) in an 8 mL sealed vial was heated at 145° C. for 48 h. The reaction vessel was cooled to room temperature. The crude product was purified by prep. HPLC to yield 2-adamantan-1-yl-N-[2-(4-fluoro-benzyl)-1-oxo-1,2-dihydro-isoquinolin-5-yl]-acetamide (0.298 g, 0.67 mmol, 75%) as a pale yellow powder.

Workup

  1. customsealed vial
  2. temperatureThe reaction vessel was cooled to room temperature
  3. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-3b16caecd50040bdb667b3491406043e
Source dataset
uspto-grants-2008_07
Patent number
US07402596B2

Reaction notes

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