Methanol → (R)-6-Chloro-N-((4,4-difluorocyclohexyl)methyl)-2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroiso-quinoline-5-carboxamide

HRID 418543Notes

Reaction equation

HRID 418543 reaction equation
C([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:30])[C:14]=2[C:18](=[O:29])[NH:19][CH2:20][CH:21]2[CH2:26][CH2:25][C:24]([F:28])([F:27])[CH2:23][CH2:22]2)[C:9]1=[O:31])[CH3:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>>[Cl:30][C:13]1[CH:12]=[CH:11][C:10]2[C:9](=[O:31])[N:8]([C@H:6]([CH3:7])[CH2:5][OH:4])[CH:17]=[CH:16][C:15]=2[C:14]=1[C:18]([NH:19][CH2:20][CH:21]1[CH2:26][CH2:25][C:24]([F:28])([F:27])[CH2:23][CH2:22]1)=[O:29]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59845735(R)-2-(6-Chloro-5-((4,4-difluorocyclohexyl)methylcarbamoyl)-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 25014111(R)-6-Chloro-N-((4,4-difluorocyclohexyl)methyl)-2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroiso-quinoline-5-carboxamide

Procedure

(R)-2-(6-Chloro-5-((4,4-difluorocyclohexyl)methylcarbamoyl)-1-oxoisoquinolin-2(1H)-yl)propyl acetate (140 mg, 0.00029 mol) and potassium carbonate (140 mg, 0.0010 mol) were stirred in methanol (6 mL, 0.1 mol) at room temperature for 1 hour, concentrated, purified by reverse phase preparative HPLC to afford the desired product as a white solid. (77 mg, 63%).

Workup

  1. concentrationconcentrated
  2. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-83d6e3cc8ee746dcb8a462ca84863439
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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