Morpholine → HCID 178487756, compound

HRID 1852239Notes

Reaction equation

HRID 1852239 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:14])[NH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CCN(C(C)C)C(C)C>C(O)CO>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5]([OH:14])=[N:4][CH:3]=[C:2]2[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 579564624-Bromo-6-methoxyisoquinolin-1(2H)-one

Product 1

HCID 178487756HCID 178487756, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a solution of 4-bromo-6-methoxyisoquinolin-1(2H)-one (0.5 g, 1.968 mmol) and morpholine (0.429 g, 4.92 mmol) in ethylene glycol (2.5 ml) was added DIPEA (1.031 ml, 5.90 mmol). The reaction was irradiated in a microwave at 145° C. for 1.5 h. The reaction mixture was adsorbed on silica was purified by silica gel chromatography (30% ethyl acetate in pet ether) to get desired compound (0.29 g, 53.8%) as solid. 1H NMR (400 MHz, CDCl3): δ ppm 10.98(s, 1H), 8.11 (s, 1H), 7.24-7.11 (m, 3H), 3.88 (s, 3H), 3.56-3.55 (m, 4H), 2.52-2.51 (m, 4H); MS: MS m/z 261 (M++1).

Workup

  1. customThe reaction was irradiated in a microwave at 145° C. for 1.5 h
  2. customwas purified by silica gel chromatography (30% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-1b5955ac81514c3480456eb23ed7ab30
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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