1,2-Dichloroethane → HCID 178452376, compound

HRID 1185593Notes

Reaction equation

HRID 1185593 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.[CH2:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29][NH2:30])[CH2:24][CH2:23]1)=[O:21])[CH2:16][CH2:17][CH3:18].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][N:25]([C:28](=[O:31])[CH2:29][NH:30][C:12]([C:4]2[CH:3]=[C:2]([OH:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[O:14])[CH2:26][CH2:27]1)=[O:21])[CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 667130634-(2-Amino-acetyl)-piperazine-1-carboxylic acid butyl esterHCID 178418933HCID 178418933, compound

Product 1

HCID 178452376HCID 178452376, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 9.5 g of 4-Hydroxy-quinoline-2-carboxylic acid and 12.2 g of 4-(2-Amino-acetyl)-piperazine-1-carboxylic acid butyl ester in 110 ml of DMF, 7.7 g of HOBT and 9.6 g of EDC was added and the reaction mixture was stirred for 16 h at RT. Then, the reaction mixture was diluted with water and extracted with DCM. The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The isolated crude product was used in the next reaction step. Yield: 23 g.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe isolated crude product
  5. customwas used in the next reaction step

Sources & evidence

ORD record
ord-1ee5a3baee454be6a10eccbbf6eade0e
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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