Ethanol → N-(7-isobutylisoquinolin-3-yl)cyclopropanecarboxamide

HRID 468756Notes

Reaction equation

HRID 468756 reaction equation
[CH3:1][C:2]([CH3:20])=[CH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:10]=[CH:11]2)=[CH:6][CH:5]=1.C(OCC)(=O)C.C(O)C>[Pd]>[CH2:3]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:10]=[CH:11]2)=[CH:6][CH:5]=1)[CH:2]([CH3:20])[CH3:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 67974264N-(7-(2-methylprop-1-enyl)isoquinolin-3-yl)cyclopropanecarboxamide

Product 1

HCID 67974896N-(7-isobutylisoquinolin-3-yl)cyclopropanecarboxamideYield 70.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

To a solution of N-(7-(2-methylprop-1-enyl)isoquinolin-3-yl)cyclopropanecarboxamide (100.0 mg, 0.2891 mmol) in ethyl acetate (10.0 mL, 102 mmol) was added palladium (30.6 mg, 0.0288 mmol) (10 wt % on carbon). The reaction vessel was purged first with nitrogen and then with hydrogen, and stirred at room temperature under a hydrogen balloon for 2 hours. Ethanol (5.0 mL, 86 mmol) and palladium (41.9 mg, 0.0394 mmol) were added, and the reaction maintained at room temperature for 19 hours. The reaction mixture was then filtered through celite and evaporated in vacuo. The crude product was purified via reverse phase HPLC and lyophilized to yield 54.4 mg (70%) of N-(7-isobutylisoquinolin-3-yl)cyclopropanecarboxamide. LCMS (ESI): RT=5.079, M+H=269.1, method=E; 1H NMR (400 MHz, DMSO-d6) δ 10.85 (s, 1H), 9.06 (s, 1H), 8.41 (s, 1H), 7.86-7.70 (m, 2H), 7.54 (dd, J=8.6, 1.3 Hz, 1H), 2.62 (d, J=7.1 Hz, 2H), 2.13-2.01 (m, 1H), 1.94 (dp, J=13.4, 6.7 Hz, 1H), 0.90 (d, J=6.6 Hz, 6H), 0.86-0.75 (m, 4H).

Workup

  1. customThe reaction vessel was purged first with nitrogen
  2. temperaturethe reaction maintained at room temperature for 19 hours
  3. filtrationThe reaction mixture was then filtered through celite
  4. customevaporated in vacuo
  5. customThe crude product was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-73b1462aa98446b6aeda1aa3f8fefa33
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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