Sodium Hydroxide → HCID 71735940, compound

HRID 1481175Notes

Reaction equation

HRID 1481175 reaction equation
C([O:3][C:4](=[O:35])[C:5]([CH3:34])([CH3:33])[CH2:6][NH:7][C:8]([C:10]1[N:11]=[C:12]([C:31]#[N:32])[C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][CH:16]=[C:15]([NH:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23])[CH:14]=2)=[O:9])C.[OH-].[Na+]>CO>[C:31]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:23])[CH:14]=2)[C:19]([OH:20])=[C:10]([C:8]([NH:7][CH2:6][C:5]([CH3:34])([CH3:33])[C:4]([OH:35])=[O:3])=[O:9])[N:11]=1)#[N:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89812939HCID 89812939, compound

Product 1

HCID 71735940HCID 71735940, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-{[1-Cyano-4-hydroxy-7-(3-phenyl-ureido)-isoquinoline-3-carbonyl]-amino}-2,2-dimethyl-propionic acid ethyl ester (35 mg, 0.0736 mmol) was methanol (5 mL) and aqueous sodium hydroxide (5 mL, 2M) was added via syringe. The reaction was permitted to stir overnight at room temperature. Upon completion, the reaction was concentrated, diluted with water and acidified to pH 3 with 1M hydrochloric acid. The resulting precipitate was isolated by filtration and dried to provide the title compound as a white solid in 73% yield. MS ESI(−) m/e: 446.0440 (M−1), MS ESI(+) m/e: 448.1482 (M+1).

Workup

  1. additionwas added via syringe
  2. concentrationUpon completion, the reaction was concentrated
  3. additiondiluted with water
  4. customThe resulting precipitate was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-2781177362cf4722919a27e334ad8100
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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