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Methanol → 6-((1S,3S)-3-Amino-cyclopentyloxy)-2H-isoquinolin-1-one

HRID 402536
Notes
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Reaction equation

HRID 402536 reaction equation
COC1C=CC(C[N:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]4[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20]4)[CH:14]=3)[C:9]2=[O:25])=CC=1.CO>C(O)(C(F)(F)F)=O>[NH2:24][C@H:21]1[CH2:22][CH2:23][C@H:19]([O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[C:9](=[O:25])[NH:8][CH:17]=[CH:16]3)[CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 887MethanolHCID 592248392-(4-Methoxy-benzyl)-6-((1S,3S)-3-amino-cyclopentyloxy)-2H-isoquinolin-1-one

Product 1

HCID 247829906-((1S,3S)-3-Amino-cyclopentyloxy)-2H-isoquinolin-1-oneYield 50.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
150 °C

Procedure

125 mg (0.34 mmol) of 2-(4-methoxy-benzyl)-6-((1S,3S)-3-amino-cyclopentyloxy)-2H-isoquinolin-1-one (39) were dissolved in 1 mL of TFA and heated in a microwave oven at 150° C. for 3 h. Methanol was added and the reaction mixture was evaporated. The solution was taken up in 1N HCl and extracted three times with dichloromethane. The combined dichloromethane layers were extracted with 1N HCl twice and the combined HCl layers were lyophilized. The residue was dissolved in water and lyophilized again to yield 42 mg of 6-((1S,3S)-3-amino-cyclopentyloxy)-2H-isoquinolin-1-one (43) as hydrochloride. Rt=0.86 min (Method E). Detected mass: 245.1 (M+H+).

Workup

  1. customthe reaction mixture was evaporated
  2. extractionextracted three times with dichloromethane
  3. extractionThe combined dichloromethane layers were extracted with 1N HCl twice
  4. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-b116c9eba4fe43db893bd5fa317c0e57
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08742116B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes