Water → HCID 68800023, compound

HRID 1370288Notes

Reaction equation

HRID 1370288 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Br:19])=[C:12]([CH2:17]Br)[CH:13]=2)[N:8]([CH2:20][C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])[CH:7]=1)=[O:5])[CH3:2].[CH3:29][NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(OCC)(=O)C.O>CCN(C(C)C)C(C)C.CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Br:19])=[C:12]([CH2:17][N:30]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH3:29])[CH:13]=2)[N:8]([CH2:20][C:21]2[C:22]([F:28])=[CH:23][CH:24]=[CH:25][C:26]=2[F:27])[CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7669N-MethylbenzylamineHCID 8857Ethyl AcetateHCID 68799492HCID 68799492, compound

Product 1

HCID 68800023HCID 68800023, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of 7-bromo-6-bromomethyl-1-(2,6-difluorobenzyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester (110 mg, 0.21 mmol), methylbenzylamine (31 mg, 0.26 mmol) in DIPEA (0.045 mL) and DMF (15 mL) was stirred at room temperature for 16 h. Ethyl acetate and water were added. The organic phase was separated and washed with water, dried with MgSO4. The solvent was evaporated and the residue dried under vacuum to yield the product as a white solid.

Workup

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried with MgSO4
  4. customThe solvent was evaporated
  5. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-6489ed3dc5b243a3bbbdd1ce0a137114
Source dataset
uspto-grants-2003_06
Patent number
US06583153B2

Reaction notes

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