1,2-Dichloroethane → HCID 178452384, compound

HRID 1970639Notes

Reaction equation

HRID 1970639 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH:10]=[C:9]([C:13]([OH:15])=O)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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].C(Cl)CCl>CN(C=O)C.CCN(C(C)C)C(C)C.C(OCC)(=O)C>[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:9]2[CH:10]=[C:11]([OH:12])[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[O:15])[CH2:27][CH2:28]1)=[O:22])[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 91673915-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylic acidHCID 66713063HCID 66713063, compound

Product 1

HCID 178452384HCID 178452384, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 2.77 g of 1-phenyl-3-carboxy-5-pyrazolone and 3.3 g 4-(2-Amino-acetyl)-piperazine-1-carboxylic acid butyl ester in 70 ml DMF 2.7 g HOBT, 5.6 ml DIPEA and 3.4 g EDC were added and the reaction mixture was stirred for 12 h at RT. Then the reaction mixture was diluted with ethyl acetate and subsequently extracted with aqueous LiCl (4% w/w), 0.1 M HCl and aqueous NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The crude product thus obtained was used in the subsequent reaction. Yield: 5.3 g.

Workup

  1. extractionsubsequently extracted with aqueous LiCl (4% w/w), 0.1 M HCl and aqueous NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-285de2842da74d3693cadef7007691fd
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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