Hydrochloric Acid → HCID 71736101, compound

HRID 1481133Notes

Reaction equation

HRID 1481133 reaction equation
C[O:2][C:3](=[O:31])[C:4]([CH3:30])([CH3:29])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([C:27]#[N:28])[C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][CH:15]=[C:14]([S:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:13]=2)=[O:8].[OH-].[Na+].Cl>CO>[C:27]([C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([S:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:13]=2)[C:18]([OH:19])=[C:9]([C:7]([NH:6][CH2:5][C:4]([CH3:30])([CH3:29])[C:3]([OH:31])=[O:2])=[O:8])[N:10]=1)#[N:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89813164HCID 89813164, compound

Product 1

HCID 71736101HCID 71736101, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[(1-cyano-4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid methyl ester (46 mg, 0.11 mmol), 2 M NaOH (2 mL) and MeOH (2 mL) was stirred at r.t. for 3 h. 1 M HCl was added until pH was ˜2, and the resulting suspension was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-25% EtOAc/hexanes+2% AcOH) to give 29 mg of the title compound. MS: (−) m/z 420.09 (M−1).

Workup

  1. extractionthe resulting suspension was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (0-25% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-8f169ea048ae47c5893ab5f2b2682640
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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