Morpholine → HCID 58767482, compound

HRID 639924Notes

Reaction equation

HRID 639924 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:15][CH:16]=2)[C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[C:10]([C:31]#[N:32])[N:9]=1>CCCCO.C(Cl)(Cl)Cl>[F:30][C:26]1[CH:25]=[C:24]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)[CH:13]=3)[C:8]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:9][C:10]=2[C:31]#[N:32])[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86609504HCID 86609504, compound

Product 1

HCID 58767482HCID 58767482, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
220 °C

Procedure

Morpholine (36 mg, 0.42 mmol) was added to a solution of 1-chloro-4-(3-fluorophenyl)-6-pyridin-2-ylisoquinoline-3-carbonitrile (15 mg, 0.04 mmol) in n-BuOH (1.0 mL) in a microwave tube. The tube was sealed and heated to 220° C. for 1 h in the microwave. The reaction was diluted with CHCl3 and washed with sat'd NaHCO3, brine, dried (MgSO4), filtered and concentrated. The residue was purified via flash chromatography (1:3-1:1 EtOAc/hexanes) to yield the title compound as a beige solid.

Workup

  1. customThe tube was sealed
  2. washwashed with sat'd NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via flash chromatography (1:3-1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-447d95ac17174b268fdc6b807b99d292
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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