Hydrochloric Acid → HCID 178487512, compound

HRID 651599Notes

Reaction equation

HRID 651599 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:17][CH2:16][C@H:15]([NH:18][S:19]([C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([O:32][CH3:33])=[CH:27][CH:28]=5)[CH:23]=4)(=[O:21])=[O:20])[C:14]3=[O:34])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[OH-:35].[Na+].Cl>O1CCOCC1>[OH:35][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:17][CH2:16][CH:15]([NH:18][S:19]([C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([O:32][CH3:33])=[CH:27][CH:28]=5)[CH:23]=4)(=[O:21])=[O:20])[C:14]3=[O:34])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 155458317-Methoxy-naphthalene-2-sulfonic acid[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(s)-yl]-amide

Product 1

HCID 178487512HCID 178487512, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-Methoxynaphthalene-2-sulfonic acid [1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide (0.07 g, 0.14 mmol), prepared as described in EXAMPLE 1, Part K, is treated with dioxane (1 mL) and 10% aq. NaOH (3 mL) and heated to reflux for 48 hours. The reaction was cooled, acidified with 1 N HCl and extracted with CH2Cl2. The organic layer is separated, dried and concentrated. The residue is purified by column chromatography eluting with 2.5% MeOH/CH2Cl2. The product fractions are collected, concentrated and precipitated with dilute HCl/ether to yield the title compound (0.041 g, 0.086 mmol).

Workup

  1. temperatureheated
  2. temperatureto reflux for 48 hours
  3. temperatureThe reaction was cooled
  4. extractionextracted with CH2Cl2
  5. customThe organic layer is separated
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is purified by column chromatography
  9. washeluting with 2.5% MeOH/CH2Cl2
  10. customThe product fractions are collected
  11. concentrationconcentrated
  12. customprecipitated with dilute HCl/ether

Sources & evidence

ORD record
ord-909cad4e41604bd6ab20d4d1fb720db6
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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