Hydrochloric Acid → HCID 86679262, compound

HRID 1519687Notes

Reaction equation

HRID 1519687 reaction equation
Cl.C[O:3][CH:4](OC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:31])[N:20]([CH:22]([C:27]([NH:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24])[CH3:21])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1>CC(C)=O>[CH:4]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:31])[N:20]([CH:22]([C:27]([NH:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24])[CH3:21])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86679263HCID 86679263, compound

Product 1

HCID 86679262HCID 86679262, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under ice cooling, a 1.0 mol/L hydrochloric acid aqueous solution (4.0 mL) was added to an acetone (50 mL) solution of 1-(dimethoxymethyl)-4-[(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)ethynyl]benzene (6.5 g) as obtained in Example 10-(4), and the mixture was stirred for 15 hours at room temperature. The solvent was distilled off, and then hexane/AcOEt (20:1 (v/v)) was added to the residue, whereafter the mixture was stirred for a while. Then, the precipitate was filtered off and dried to obtain 1-formyl-4-[(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)ethynyl]benzene (white solid) (4.6 g, 79%).

Workup

  1. customas obtained in Example 10-(4)
  2. distillationThe solvent was distilled off
  3. additionhexane/AcOEt (20:1 (v/v)) was added to the residue, whereafter the mixture
  4. stirringwas stirred for a while
  5. filtrationThen, the precipitate was filtered off
  6. customdried

Sources & evidence

ORD record
ord-b989be78ae20476e94b8f461face9191
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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