Methylamine → HCID 57646789, compound

HRID 1022883Notes

Reaction equation

HRID 1022883 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21](Cl)=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][NH2:27]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([NH:27][CH3:26])=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 57647050HCID 57647050, compound

Product 1

HCID 57646789HCID 57646789, compound

Procedure

154 mg (0.42 mmol) of 4-(1-Chloro-isoquinolin-6-yloxy)-piperidine-1-carbocyclic acid tert-butyl ester (162) were heated in 15 ml of an aqueous methylamine-solution (41%)) at 110° C. in a sealed tube. After 7 h the reaction mixture was evaporated and the residue was taken up in saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate and the solvent was removed i. vac. The residue was purified by silica gel chromatography (ethyl acetate/methanol 5:1). Yield: 45 mg. Rt=1.14 min (Method #4). Detected mass: 358.3 (M+H+).

Workup

  1. customAfter 7 h the reaction mixture was evaporated
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed i
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/methanol 5:1)

Sources & evidence

ORD record
ord-44cf9dcb6c4640b296c221119e6e3ead
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Reaction notes

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