Sodium Hydroxide → HCID 89813139, compound

HRID 1481061Notes

Reaction equation

HRID 1481061 reaction equation
C([O:3][C:4](=[O:34])[C:5]([CH3:33])([CH3:32])[CH2:6][NH:7][C:8]([C:10]1[N:11]=[C:12]([C:30]#[N:31])[C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][CH:16]=[C:15]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH3:29])[CH:14]=2)=[O:9])C.[OH-].[Na+]>O1CCCC1.CO>[C:30]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:28][CH3:29])[CH:14]=2)[C:19]([OH:20])=[C:10]([C:8]([NH:7][CH2:6][C:5]([CH3:32])([CH3:33])[C:4]([OH:34])=[O:3])=[O:9])[N:11]=1)#[N:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89813081HCID 89813081, compound

Product 1

HCID 89813139HCID 89813139, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-{[1-Cyano-7-(2-ethyl-phenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid ethyl ester (20.3 mg, 0.04 mmole) and 1N NaOH (0.4 ml, 0.4 mmole) in a mixture of tetrahydrofuran (0.5 ml) and methanol (1 ml) was stirred room temperature for three days before it was concentrated and acidified with 1N HCl to pH=3. The precipitated was filtered, dried to give the title compound as a white solid (15 mg): MS: (+) m/z 434.21 (M+1), (−) m/z 432.15 (M−1).

Workup

  1. concentrationwas concentrated
  2. filtrationThe precipitated was filtered
  3. customdried

Sources & evidence

ORD record
ord-409af33cba114253aa77291f8e56084a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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