Hydrochloric Acid → 2-[3-Chloro-5-(3-[(dimethylamino)methyl]phenethylamino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetic acid hydrochloride

HRID 567809

Reaction equation

HRID 567809 reaction equation
C([O:8][C:9](=[O:33])[CH2:10][N:11]1[C:16](=[O:17])[C:15]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:28]([CH3:30])[CH3:29])[CH:22]=2)=[N:14][C:13]([Cl:31])=[C:12]1[CH3:32])C1C=CC=CC=1.Cl>C(O)C.[Pd]>[ClH:31].[Cl:31][C:13]1[N:14]=[C:15]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:28]([CH3:30])[CH3:29])[CH:22]=2)[C:16](=[O:17])[N:11]([CH2:10][C:9]([OH:33])=[O:8])[C:12]=1[CH3:32]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18470815Benzyl 2-[3-chloro-5-(3-[(dimethylamino)methyl]phenethylamino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate

Product 1

HCID 699631282-[3-Chloro-5-(3-[(dimethylamino)methyl]phenethylamino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl-2-[3-chloro-5-(3-[(dimethylamino)methyl]phenethylamino)-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 20) (100 mg, 0.21 mmol) was dissolved in ethanol (10 ml), treated with 10% Pd on carbon catalyst (20 mg), aq HCl (1 m, 0.1 ml) and stirred under a hydrogen atmosphere (20 psi, room temperature, 2 hr). The catalyst was removed by filtration, the solvent evaporated to dryness and the residue azeotroped with CH2Cl2 to give the desired product, slightly impure (white solid, 85 mg). 1H NMR (CD3OD) δ 2.30 (s, 3H), 2.80 (s, 6H), 3.00 (t, 2H), 3.60 (t, 2H), 4.20 (s, 2H), 4.70 (s, 2H), 7.30 (m, 2H), 7.40 (m, 2H). LRMS m/z=379.1 (M+1)+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated to dryness
  3. customthe residue azeotroped with CH2Cl2

Sources & evidence

ORD record
ord-89a0ea69270b4ec58d0bbbf0a6c06ac9
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Linked notes

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