Cesium carbonate → HCID 68599959, compound

HRID 1185556Notes

Reaction equation

HRID 1185556 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[CH:9][C:10]([CH3:18])=[C:11]([Cl:17])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:25]1([NH:29][C:30]([C@@H:32]2[CH2:36][CH2:35][CH2:34][N:33]2[C:37](=[O:40])[CH2:38]Br)=[O:31])[CH2:28][CH2:27][CH2:26]1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][CH2:38][C:37]([N:33]2[CH2:34][CH2:35][CH2:36][C@H:32]2[C:30](=[O:31])[NH:29][CH:25]2[CH2:28][CH2:27][CH2:26]2)=[O:40])[C:13]2[C:8](=[CH:9][C:10]([CH3:18])=[C:11]([Cl:17])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 68600332HCID 68600332, compound2×HCID 178469290HCID 178469290, compound

Product 1

HCID 68599959HCID 68599959, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1.1 g 6-Chloro-4-hydroxy-7-methyl-quinoline-2-carboxylic acid ethyl ester in 25 ml DMF were added 2.7 g of cesium carbonate followed by dropwise addition of a solution of 1.8 g (S)-1-(2-Bromo-acetyl)-pyrrolidine-2-carboxylic acid cyclobutylamide in 25 ml DMF over a period of 3 h. After this time another portion of cesium carbonate (700 mg) and (S)-1-(2-Bromo-acetyl)-pyrrolidine-2-carboxylic acid cyclobutylamide (700 mg) were added over 1.5 h. The mixture was evaporated, diluted with DCM and washed with aqueous LiCl (4%). The crude product obtained after evaporation of the solvent was pure enough for the subsequent transformation. Yield: 3.3 g.

Workup

  1. customThe mixture was evaporated
  2. additiondiluted with DCM
  3. washwashed with aqueous LiCl (4%)

Sources & evidence

ORD record
ord-a34f0cfe336c4f06957bad36b090c86c
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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