(9H-fluoren-9-yl)methyl 2-(5-bromo-2-carbamoylphenylcarbamoyl)pyrrolidine-1-carboxylate → (9H-fluoren-9-yl)methyl 2-(7-bromo-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate

HRID 1619344Notes

Reaction equation

HRID 1619344 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[C:23](=O)[NH:24][C:25]3[CH:30]=[C:29]([Br:31])[CH:28]=[CH:27][C:26]=3[C:32](=[O:34])[NH2:33])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>O=S(Cl)Cl>[Br:31][C:29]1[CH:30]=[C:25]2[C:26]([C:32](=[O:34])[NH:33][C:23]([CH:19]3[CH2:20][CH2:21][CH2:22][N:18]3[C:16]([O:15][CH2:14][CH:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)=[O:17])=[N:24]2)=[CH:27][CH:28]=1

Participants

3

Reactant 1

HCID 58574511(9H-fluoren-9-yl)methyl 2-(5-bromo-2-carbamoylphenylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 136038175(9H-fluoren-9-yl)methyl 2-(7-bromo-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylateYield 31.3%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of (9H-fluoren-9-yl)methyl-2-(5-bromo-2-carbamoylphenylcarbamoyl)pyrrolidine-1-carboxylate (0.55 g, 0.94 mmol) in excess SOCl2 was stirred at room temperature. After pouring into ice water, the mixture was adjusted to pH 7.0, extracted with ethyl acetate (3×100 mL) and concentrated to give the crude product. 152 mg of the desired product was obtained by column chromatography. MS (ESI): 516, 518 (MH+)

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. concentrationconcentrated
  3. customto give the crude product

Sources & evidence

ORD record
ord-61cc443d40fd491b9efc9bcb5bcca43f
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

Loading…