N-bromobutanimide → HCID 86689498, compound

HRID 1853803Notes

Reaction equation

HRID 1853803 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:31]=[CH:30][C:20]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:19][CH:18]=1.[Br:32]N1C(=O)CCC1=O>CN(C=O)C>[Br:32][C:11]1[C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]([C:17]2[CH:31]=[CH:30][C:20]([CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:19][CH:18]=2)=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67447234HCID 67447234, compound

Product 1

HCID 86689498HCID 86689498, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzylcarbamate (29 mg, 0.055 mmol) in DMF (1 mL) was added N-bromosuccinimide (12 mg, 0.066 mmol) and the reaction was stirred at room temperature for 1 h and heated at 50° C. for 2 h. The reaction mixture was concentrated and the residue was purified by preparatory TLC (silica, methanol/methylene chloride gradient) to afford the desired product (10 mg, 35%): ESI MS m/z 516 [C24H23BrN2O4S+H]+.

Workup

  1. temperatureheated at 50° C. for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by preparatory TLC (silica, methanol/methylene chloride gradient)

Sources & evidence

ORD record
ord-d88b5f7d378a435fb1ae386e9342dd37
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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