Hydrochloric Acid → HCID 117844047, compound

HRID 1481016Notes

Reaction equation

HRID 1481016 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:24])=[C:5]([C:25]([NH:27][CH2:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32]CC)=[O:31])=[O:26])[N:4]=1)#[N:2].O.CCOC(C)=O.Cl>CO.[OH-].[Na+]>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:24])=[C:5]([C:25]([NH:27][CH2:28][C:29]([CH3:36])([CH3:35])[C:30]([OH:32])=[O:31])=[O:26])[N:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 89812965HCID 89812965, compound

Product 1

HCID 117844047HCID 117844047, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 3-(1-cyano-4-hydroxy-7-(naphthalen-1-yloxy)isoquinoline-3-carboxamido)-2,2-dimethylpropanoate (16 mg, 0.03 mmol) was dissolved in MeOH (4 mL) and 2 N NaOH (4 mL). After stirring for 5 hours at room temperature, H2O (15 mL) and EtOAc (15 mL) were added. To the stirred mixture was added 1 N hydrochloric acid until pH was 1. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% MeOH/CH2Cl2) to give the title compound in 13 mg. MS: (−) m/z 454.03 (M−1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by flash chromatography (0-30% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-acf1d41fe9944e138bafffa4ecf34ed0
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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