Diisopropylethylamine → HCID 70978322, compound

HRID 1852241Notes

Reaction equation

HRID 1852241 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.[CH3:15][C@@H:16]1[O:21][C@H:20]([CH3:22])[CH2:19][NH:18][CH2:17]1.CCN(C(C)C)C(C)C>C(O)CO>[CH3:22][CH:20]1[CH2:19][N:18]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=3)[C:5](=[O:14])[NH:4][CH:3]=2)[CH2:17][CH:16]([CH3:15])[O:21]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6415002,6-Dimethylmorpholine, cis-HCID 579564624-Bromo-6-methoxyisoquinolin-1(2H)-one

Product 1

HCID 70978322HCID 70978322, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a solution of 4-bromo-6-methoxyisoquinolin-1(2H)-one (0.2 g, 0.787 mmol) and (2S,6R)-2,6-dimethylmorpholine (0.181 g, 1.574 mmol) in ethylene glycol (2.5 ml) was added DIPEA (0.412 ml, 2.361 mmol). The reaction was irradiated in 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 (0.11 g, 48.5%) as solid. MS: MS m/z 289.18 (M++1).

Workup

  1. customThe reaction was irradiated in 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-af14e589b33c49aaa0b7d3fd072e31cd
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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