Triethylamine → HCID 57855384, compound

HRID 547381Notes

Reaction equation

HRID 547381 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:21]([NH:22][CH3:23])=[CH:20][CH:19]=[CH:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1.[CH3:26][S:27]([CH2:30][C:31](Cl)=[O:32])(=[O:29])=[O:28].C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[C:21]([N:22]([CH3:23])[C:31](=[O:32])[CH2:30][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:20][CH:19]=[CH:18][N:13]3[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 21288095(Methanesulfonyl)acetyl chloride2×HCID 54730630N-[(4-fluorophenyl)methyl]-3-hydroxy-9-(methylamino)-4-oxo-pyrido[1,2-a]pyrimidine-2-carboxamide

Product 1

HCID 57855384HCID 57855384, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-fluorobenzyl)-3-hydroxy-9-(methylamino)-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxamide was dissolved in dichloromethane. Methylsulfonylacetyl chloride (1.2 eqs.) and triethylamine (2 eqs.) were added and the solution was stirred at room temperature. After 5 hours a further 2 eqs. of methylsulfonylacetyl chloride and 2 eqs. of triethylamine were added. The solvent was removed under vacuum and the residue was suspended in methano/0.1 M NaOH. The suspension was sonicated for 2 minutes and left stirring at room temperature for 30 minutes. The product was purified by preparative RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluants (column: C18). The product was obtained after lyophilization of the pooled product fractions as bright yellow fluffy material.

Workup

  1. customThe solvent was removed under vacuum
  2. customThe suspension was sonicated for 2 minutes
  3. waitleft
  4. stirringstirring at room temperature for 30 minutes
  5. customThe product was purified by preparative RP-HPLC
  6. customThe product was obtained after lyophilization of the pooled product fractions as bright yellow fluffy material

Sources & evidence

ORD record
ord-57e924651afc447291c5125d851a582b
Source dataset
uspto-grants-2011_05
Patent number
US07939537B2

Reaction notes

Loading…