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Methanol → HCID 178484836, compound

HRID 1913141
Notes
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Reaction equation

HRID 1913141 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][CH:19]4[CH2:24][CH2:23][CH:22]([NH:25][CH3:26])[CH2:21][CH2:20]4)[CH:14]=3)[C:9]2=[O:27])=CC=1.CO>C(O)(C(F)(F)F)=O>[CH3:26][NH:25][C@H:22]1[CH2:23][CH2:24][C@H:19]([O:18][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[C:9](=[O:27])[NH:8][CH:17]=[CH:16]3)[CH2:20][CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 887MethanolHCID 584680822-(4-methoxy-benzyl)-6-(4-methylamino-cyclohexyloxy)-2H-isoquinolin-1-one

Product 1

HCID 178484836HCID 178484836, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
150 °C

Procedure

2.46 g of 2-(4-methoxy-benzyl)-6-(4-methylamino-cyclohexyloxy)-2H-isoquinolin-1-one (151) were dissolved in 15 mL of TFA and heated in a microwave oven at 150° C. for 2 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 taken up in water and lyophilized again to yield 1.31 g of 6-(4-methylamino-cyclohexyloxy)-2H-isoquinolin-1-one (152) as hydrochloride. Rt=0.81 min (Method B). Detected mass: 273.2 (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

Sources & evidence

ORD record
ord-91a52b4baefe47eab60cfd81f1596ef0
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08609691B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes