Triethylamine → HCID 67794289, compound

HRID 1034235Notes

Reaction equation

HRID 1034235 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[NH2:14][CH:15]1[C:19](=[O:20])[N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH2:17][CH:16]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C(N(CC)CC)C>C(Cl)Cl>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:18]1[C:19](=[O:20])[C@H:15]([NH:14][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[O:12])[C@H:16]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 19023603HCID 19023603, compound

Product 1

HCID 67794289HCID 67794289, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-naphthoyl chloride (178 mg, 0.934 mmol) in CH2Cl2 (3 ml) was added a solution of aminopyrrolidinone of Example W (250 mg, 0.849 mmol) and triethylamine (146 mg, 1.44 mmol) in CH2Cl2 (3 ml) and the resulting solution was stirred at room temperature for 18 h. The solvent was then removed in vacuo and the resulting foam was purified by radial chromatography on a silica gel plate (4 mm) eluting with 2/98 EtOH/CH2Cl2 to give the title compound (380 mg, 100%) as a colorless foam. MS M+1 calcd for C26H25N2O4F 449, found 449. DSC =142.2°-151.5° [email protected] J/g.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe resulting foam was purified by radial chromatography on a silica gel plate (4 mm)
  3. washeluting with 2/98 EtOH/CH2Cl2

Sources & evidence

ORD record
ord-b219e8cb550349f599615f5a26c15013
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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