Water → HCID 10253527, compound

HRID 1987025Notes

Reaction equation

HRID 1987025 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:19])[N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:3]=1.[NH2:27][CH:28]([CH2:31][OH:32])[CH2:29][OH:30].O>CN1C(=O)CCC1>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:9]1[C:10]2[C:5](=[C:4]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[N:3]=[C:2]([NH:27][CH:28]([CH2:31][OH:32])[CH2:29][OH:30])[CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 68294SerinolHCID 10321326HCID 10321326, compound

Product 1

HCID 10253527HCID 10253527, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7-Bromo-1,5-bis(2-chlorophenyl)[1,6]naphthyridin-2(1H)-one (38 mg, 0.085 mmol) was dissolved in NMP (2 ml) and serinol (2-amino-1,3-propanediol) (35 mg, 0.384 mmol) added, and the solution heated in a Smith creator microwave at 220° for 0.5 h. After cooling, the solution was added to water (12 ml) and extracted with dichloromethane (10 ml). The mixture was passed through a hydrophobic frit and evaporated in vacuo. The residue was purified by SPE (SiO2, 10 g) eluting with dichloromethane-methanol (98:2) to afford the title compound as a gum (9 mg, 23%).

Workup

  1. temperaturethe solution heated in a Smith creator microwave at 220° for 0.5 h
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane (10 ml)
  4. customevaporated in vacuo
  5. customThe residue was purified by SPE (SiO2, 10 g)
  6. washeluting with dichloromethane-methanol (98:2)

Sources & evidence

ORD record
ord-14d5fe59f65544618b8d5fd5ac26fbba
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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