N-methyl-2-pyrrolidone → HCID 68987357, compound

HRID 1987039Notes

Reaction equation

HRID 1987039 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH2:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[CH:3]=1.[NH2:26][CH:27]([CH2:30][OH:31])[CH2:28][OH:29].CN1CCCC1=[O:38]>>[CH:30]([OH:31])=[O:38].[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:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[CH:3]=[C:2]([NH:26][CH:27]([CH2:30][OH:31])[CH2:28][OH:29])[N:11]=2)[CH:6]=[CH:7][C:8]1=[O:38]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 68294SerinolHCID 86607814HCID 86607814, compound

Product 1

HCID 68987357HCID 68987357, compoundYield 36%

Procedure

7-chloro-1,5-bis(2-chlorophenyl)[1,8]naphthyridin-2(1 h-one (73 mg, 0.182 mmol) and serinol (75 mg, 0.823 mmol) were dissolved in N-methylpyrrolidinone (2 ml) and heated in a Smith Creator microwave at 220° for 30 min. The mixture was evaporated in vacuo using a vacuum centrifuge, and the residue purified by mass directed autoprep HPLC (per general procedure B) to afford the title compound as a white solid (33 mg, 36%) NMR (400 MHz, CDCl3) δ 7.65-7.55 (2H,m), 7.52-7.42 (4H,m), 7.40-7.29 (3H,m), 6.40 (1H,s), 6.35 (1H,dd), 3.55-3.42 (5H,m)

Workup

  1. temperatureheated in a Smith Creator microwave at 220° for 30 min
  2. customThe mixture was evaporated in vacuo
  3. customthe residue purified by mass

Sources & evidence

ORD record
ord-a41b4463d6a84c4da67b03e08bd485d6
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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