N-methyl-2-pyrrolidone → HCID 68989387, compound

HRID 1987040Notes

Reaction equation

HRID 1987040 reaction equation
Cl[C:2]1[N: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])[CH:3]=1.[CH:27]([NH:30][CH2:31][CH2:32][NH2:33])([CH3:29])[CH3:28].CN1CCCC1=[O:40]>>[CH:8]([OH:19])=[O:40].[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])[CH:3]=[C:2]([NH:33][CH2:32][CH2:31][NH:30][CH:27]([CH3:29])[CH3:28])[N:11]=2)[CH:6]=[CH:7][C:8]1=[O:19]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 88098N-IsopropylethylenediamineHCID 57723000HCID 57723000, compound

Product 1

HCID 68989387HCID 68989387, compoundYield 26%

Procedure

7-chloro-1,5-bis(2-chlorophenyl)[1,8]naphthyridin-2(1H)-one (73 mg, 0.182 mmol) and N-isopropylethylenediamine (0.14 ml, 1.122 mmol) were dissolved in N-methylpyrrolidinone (2 ml) and heated in a Smith Creator microwave at 220° for 30 min. The solution was passed down an SCX-2 cartridge (10 g) and eluted with methanol, followed by 2M ammonia in methanol. The latter eluate was evaporated in vacuo and the residue purified by mass directed autoprep HPLC (per General procedure B) to afford the title compound as a clear gum (24 mg, 26%)

Workup

  1. temperatureheated in a Smith Creator microwave at 220° for 30 min
  2. washeluted with methanol
  3. customThe latter eluate was evaporated in vacuo
  4. customthe residue purified by mass

Sources & evidence

ORD record
ord-00bcfac814a947b3801d4807ffaea911
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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