4-Methylmorpholine → 2-Adamantan-1-yl-N-(2-benzyl-1-oxo-1,2-dihydro-isoquinolin-5-yl)-acetamide

HRID 749210Notes

Reaction equation

HRID 749210 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]2=[O:12].CN1CCOCC1.[C:27]12([CH2:37][C:38](Cl)=[O:39])[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2>O1CCOCC1>[C:27]12([CH2:37][C:38]([NH:1][C:2]3[CH:11]=[CH:10][CH:9]=[C:8]4[C:3]=3[CH:4]=[CH:5][N:6]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]4=[O:12])=[O:39])[CH2:34][CH:33]3[CH2:32][CH:31]([CH2:30][CH:29]([CH2:35]3)[CH2:28]1)[CH2:36]2

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27718821-Adamantaneacetyl chlorideHCID 184445335-amino-2-benzylisoquinolin-1(2H)-one

Product 1

HCID 250637642-Adamantan-1-yl-N-(2-benzyl-1-oxo-1,2-dihydro-isoquinolin-5-yl)-acetamideYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 5-amino-2-benzylisoquinolin-1(2H)-one (50 mg, 0.2 mmol) and NMM (0.022 mL, 0.2 mmol) in 1,4-dioxane (3 mL) was added dropwise at room temperature a solution of 1-adamantaneacetic acid chloride (43 mg, 0.2 mmol) in 1,4-dioxane (5 mL). The reaction mixture was stirred at room temperature for 1 h. The volatiles were removed on a rotary evaporator. The crude product was purified by prep. HPLC affording 2-Adamantan-1-yl-N-(2-benzyl-1-oxo-1,2-dihydro-isoquinolin-5-yl)-acetamide (45.5 mg, 0.11 mmol, 53% yield) as a white solid.

Workup

  1. customThe volatiles were removed on a rotary evaporator
  2. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-d5f3cfbd938a49fda41d7ba9c7dc4850
Source dataset
uspto-grants-2008_07
Patent number
US07402596B2

Reaction notes

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