Hydrochloric Acid → HCID 11494043, compound

HRID 2221450Notes

Reaction equation

HRID 2221450 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][CH2:13][C:14]#[C:15][C:16]1[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][CH:17]=1)=[O:11].[NH2:26][OH:27].[OH-].[Na+].Cl>C1COCC1.CO>[OH:27][NH:26][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:16]([C:15]#[C:14][CH2:13][NH:12][C:10]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)=[O:11])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 69199699HCID 69199699, compound

Product 1

HCID 11494043HCID 11494043, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[3-(benzothiophen-2-ylcarbonylamino)prop-1-ynyl]-benzoate (0.5 mmol) in THF/methanol (10 ml/10 ml) was added 50 wt. % aqueous hydroxylamine (3 ml) followed by 1M aqueous NaOH (1 ml) adjusting the pH to 10-11. The reaction mixture was stirred for ˜14 h, neutralized to pH=7-8 with 6M aqueous HCl, and concentrated in vacuo. The precipitate was collected and purified by HPLC providing the title compound as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe precipitate was collected
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-3295a4b43d064535b4765bbedaadf14b
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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