Cesium carbonate → 4-{2-[(4-Benzyloxycarbonylmethoxy-6,7-dimethyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester

HRID 1185542Notes

Reaction equation

HRID 1185542 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:32])[CH2:15][NH:16][C:17]([C:19]2[CH:28]=[C:27]([OH:29])[C:26]3[C:21](=[CH:22][C:23]([CH3:31])=[C:24]([CH3:30])[CH:25]=3)[N:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:39]([O:46][C:47](=[O:50])[CH2:48]Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C.O>[CH2:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:32])[CH2:15][NH:16][C:17]([C:19]2[CH:28]=[C:27]([O:29][CH2:48][C:47]([O:46][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:50])[C:26]3[C:21](=[CH:22][C:23]([CH3:31])=[C:24]([CH3:30])[CH:25]=3)[N:20]=2)=[O:18])[CH2:12][CH2:13]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 178452378HCID 178452378, compound

Product 1

HCID 686007374-{2-[(4-Benzyloxycarbonylmethoxy-6,7-dimethyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 250 mg 4-{2-[(4-Hydroxy-6,7-dimethyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester in 1.5 ml of DMF, 202 mg of cesium carbonate and 142 mg of Bromo-acetic acid benzyl ester were added and the reaction mixture was stirred for 12 h at RT. Then, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The isolated crude product was pure enough for the next reaction step. Yield: 290 mg.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe isolated crude product
  5. customwas pure enough for the next reaction step

Sources & evidence

ORD record
ord-88436633cd8444dc870b7d22b14b0d6b
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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