N-Methylbenzylamine → HCID 9917173, compound

HRID 1006481Notes

Reaction equation

HRID 1006481 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][CH:21]=3)[C:13]=2[CH2:17]Cl)[N:8]([CH2:30][C:31]2[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=2[F:38])[CH:7]=1)=[O:5])[CH3:2].[CH3:39][NH:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][CH:21]=3)[C:13]=2[CH2:17][N:40]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH3:39])[N:8]([CH2:30][C:31]2[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:32]=2[F:38])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 60109500HCID 60109500, compound

Product 1

HCID 9917173HCID 9917173, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

78 mg of 6-(4-acetamidophenoxy)-5-(chloromethyl)-1-(2′,6′-difluorobenzyl)-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid-ethyl ester, dissolved in 3 ml of dimethylformamide, was mixed with 84 μl of N-methylbenzylamine and 84 μl of N,N-diisopropyl-ethylamine at 0° C. and stirred at room temperature for 20 hours. After 20 ml of aqueous sodium bicarbonate solution was added, the precipitate was suctioned off, washed with water and then with n-hexane, and dried at room temperature in a vacuum. 70 mg of the title compound is obtained.

Workup

  1. washwashed with water
  2. dry with materialwith n-hexane, and dried at room temperature in a vacuum

Sources & evidence

ORD record
ord-58270bc044874230a445950ef48b2b15
Source dataset
uspto-grants-2004_09
Patent number
US06790858B2

Reaction notes

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