Tetrahydrofuran → HCID 71735296, compound

HRID 1481227Notes

Reaction equation

HRID 1481227 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][C@@H:5]([NH:12][C:13]([C:15]1[N:16]=[C:17]([C:33]#[N:34])[C:18]2[C:23]([C:24]=1[OH:25])=[CH:22][CH:21]=[C:20]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:19]=2)=[O:14])[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.O1CCCC1.[OH-].[Na+]>CO>[C:33]([C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[C:20]([O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:19]=2)[C:24]([OH:25])=[C:15]([C:13]([NH:12][C@@H:5]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:4][C:3]([OH:35])=[O:2])=[O:14])[N:16]=1)#[N:34]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 89812870HCID 89812870, compound

Product 1

HCID 71735296HCID 71735296, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(R)-[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-3-pyridin-3-yl-propionic acid methyl ester (25 mg, 0.0533 mmol) was dissolved in methanol (2 mL) and tetrahydrofuran (2 mL.) Sodium hydroxide solution (2 mL, 2M) was added and the reaction was permitted to stir overnight at room temperature. After 18 hours, the pH was adjusted to 4 and reaction lyophilized. The crude product was purified by HPLC to provide the title compound in 80% yield. LC-MS ESI+: 455 (M+1)+; ESI−: 453 (M−1)−.

Workup

  1. waitAfter 18 hours
  2. customthe pH was adjusted to 4 and reaction
  3. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-fd9689a3f9974f468822d360e040620b
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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