Hydrochloric Acid → HCID 69161761, compound

HRID 459867Notes

Reaction equation

HRID 459867 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:39]=[CH:38][C:28]([C:29]([NH:31][CH2:32][C:33]([O:35]CC)=[O:34])=[O:30])=[CH:27][CH:26]=4)[CH2:21][CH2:20]3)=[O:18])[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl>>[OH2:2].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]([N:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:26]=[CH:27][C:28]([C:29]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])=[CH:38][CH:39]=4)[CH2:23][CH2:24]3)=[O:18])[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86594430HCID 86594430, compound

Product 1

HCID 69161761HCID 69161761, compoundYield 77%

Procedure

To 233 mg of ethyl [(4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}benzoyl)amino]acetate was added 0.8 ml of conc. hydrochloric acid, followed by overnight stirring at room temperature. After the reaction solution was concentrated under reduced pressure, crystallization was carried out from 2-propanol-diisopropyl ether to collect [(4-f4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}benzoyl)amino]acetic acid hydrochloride by filtration. The filtrate was concentrated under reduced pressure, and the residue was crystallized from hexane to obtain 88 mg of [(4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}benzoyl)amino]acetic acid hydrate as pale brown crystals.

Workup

  1. concentrationAfter the reaction solution was concentrated under reduced pressure, crystallization
  2. customto collect [(4-f4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}benzoyl)amino]acetic acid hydrochloride
  3. filtrationby filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-121e64e422da4ba6933818bbd6c26f5b
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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