1,2-Dichloroethane → HCID 178452377, compound

HRID 1185489Notes

Reaction equation

HRID 1185489 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([OH:15])=O)[CH:3]=1.[CH2:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([C:29](=[O:32])[CH2:30][NH2:31])[CH2:25][CH2:24]1)=[O:22])[CH2:17][CH2:18][CH3:19].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.O>[CH2:16]([O:20][C:21]([N:23]1[CH2:24][CH2:25][N:26]([C:29](=[O:32])[CH2:30][NH:31][C:13]([C:4]2[CH:3]=[C:2]([OH:1])[C:11]3[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=3)[N:5]=2)=[O:15])[CH2:27][CH2:28]1)=[O:22])[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 66713063HCID 66713063, compoundHCID 178418698HCID 178418698, compound

Product 1

HCID 178452377HCID 178452377, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.0 g of 4-Hydroxy-7-methyl-quinoline-2-carboxylic acid and 7 g of 4-(2-Amino-acetyl)-piperazine-1-carboxylic acid butyl ester in 40 ml of DMF, 3.3 g of HOBT and 4.1 g of EDC was added and the reaction mixture was stirred for 4 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: 4.5 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-387a8a759cb9437f812e753fb62d122e
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

Loading…