Morpholine → HCID 70978356, compound

HRID 1852256Notes

Reaction equation

HRID 1852256 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:15])[NH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>C(O)CO.O>[F:14][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:3][NH:4][C:5]2=[O:15])=[CH:10][C:9]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 70979087HCID 70979087, compound

Product 1

HCID 70978356HCID 70978356, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-bromo-7-fluoro-6-methoxyisoquinolin-1(2H)-one (0.5 g, 1.838 mmol) and morpholine (0.4 g, 4.59 mmol) in ethylene glycol (2.5 ml) was added DIPEA (1.031 ml, 5.90 mmol). The reaction was irradiated in microwave at 145° C. for 1.5 h. The reaction was cooled to ambient temperature and diluted with water. The aqueous layer was extracted with EtOAc. The organic layer was washed with 1N HCl, followed by washing with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get the crude compound. The crude compound (0.25 g, 31.8%) was taken to the next step without further purification. MS: MS m/z 279.22 (M++1).

Workup

  1. customThe reaction was irradiated in microwave at 145° C. for 1.5 h
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with 1N HCl
  4. washby washing with brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b14cb6eaa0a645208835c82996b2b082
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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