Triethylamine → N-[4-Methanesulphonamidophenacyl]-N-methyl-2-(4-methyl-2H-phthalazin-1-on-2-yl)ethylamine hemihydrate

HRID 1196540Notes

Reaction equation

HRID 1196540 reaction equation
Br.[CH3:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]([CH2:14][CH2:15][NH:16][CH3:17])[N:4]=1.[CH3:18][S:19]([NH:22][C:23]1[CH:32]=[CH:31][C:26]([C:27](=[O:30])[CH2:28]Br)=[CH:25][CH:24]=1)(=[O:21])=[O:20].C(N(CC)CC)C>C(O)C>[OH2:13].[CH3:18][S:19]([NH:22][C:23]1[CH:32]=[CH:31][C:26]([C:27](=[O:30])[CH2:28][N:16]([CH2:15][CH2:14][N:5]2[N:4]=[C:3]([CH3:2])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:13])[CH3:17])=[CH:25][CH:24]=1)(=[O:21])=[O:20].[CH3:18][S:19]([NH:22][C:23]1[CH:32]=[CH:31][C:26]([C:27](=[O:30])[CH2:28][N:16]([CH2:15][CH2:14][N:5]2[N:4]=[C:3]([CH3:2])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:13])[CH3:17])=[CH:25][CH:24]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15592151N-(4-(2-bromoacetyl)phenyl)methanesulfonamideHCID 198989332-(4-Methyl-2H-phthalazin-1-on-2-yl)-N-methylethylamine hydrobromide

Product 1

HCID 131716101N-[4-Methanesulphonamidophenacyl]-N-methyl-2-(4-methyl-2H-phthalazin-1-on-2-yl)ethylamine hemihydrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-Methyl-2H-phthalazin-1-on-2-yl)-N-methylethylamine hydrobromide (2 g), 4-methanesulphonamidophenacyl bromide (1.8 g) and triethylamine (1.5 g) in ethanol (50 ml) were stirred at room temperature for 2 hours. The solvent was removed, the residue taken up in methylene chloride (100 ml), washed (aqueous sodium bicarbonate), dried (MgSO4) and evaporated. Chromatography on silica [Merck `Kieselgel 60` (Trade Mark)] eluting with methylene chloride containing methanol (0% up to 5%) gave, after collection and evaporation of appropriate fractions, an oil which was triturated with ethanol to give the title compound, yield 1.63 g, m.p. 176°-179°.

Workup

  1. customThe solvent was removed
  2. washwashed (aqueous sodium bicarbonate)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. washChromatography on silica [Merck `Kieselgel 60` (Trade Mark)] eluting with methylene chloride
  6. additioncontaining methanol (0% up to 5%)
  7. customgave
  8. customafter collection and evaporation of appropriate fractions
  9. customan oil which was triturated with ethanol

Sources & evidence

ORD record
ord-a389401727204960a2fb5c1357c33315
Source dataset
uspto-grants-1992_05
Patent number
US05114952

Reaction notes

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