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1,2-Dichloroethane → HCID 178452377, compound

HRID 1185596
Notes
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Reaction equation

HRID 1185596 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 667130634-(2-Amino-acetyl)-piperazine-1-carboxylic acid butyl esterHCID 178418698HCID 178418698, compound

Product 1

HCID 178452377HCID 178452377, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6.0 g of 4-Hydroxy-7-methyl-quinoline-2-carboxylic acid and 7.1 g of 4-(2-Amino-acetyl)-piperazine-1-carboxylic acid butyl ester in 61 ml of DMF, 8.5 g NEM, 5.0 g of HOBT and 6.2 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: 10.7 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-0b6678b8bf054d209e2fe6a11e0001f1
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08669266B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes