1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178480668, compound

HRID 659798Notes

Reaction equation

HRID 659798 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:14]([OH:16])=O)=[N:11][NH:12][CH:13]=1.[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:14]([C:10]3[C:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])=[CH:13][NH:12][N:11]=3)=[O:16])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2776493[4-(4-Methylpiperazin-1-yl)phenyl]methanamineHCID 178524946HCID 178524946, compound

Product 1

HCID 178480668HCID 178480668, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(2,4-dichloro-phenyl)-1H-pyrazole-3-carboxylic acid (70 mg; 0.27 mmol), 4-(4-methyl-piperazin-1-yl)-benzylamine (62 mg; 0.3 mmol), EDAC (63 mg; 0.33 mmol) and HOBt (45 mg; 0.33 mmol) in 5 ml of DMF was stirred at room temperature for 48 hours. The reaction was evaporated and the residue partitioned between ethyl acetate and brine. The ethyl acetate layer was separated, dried (MgSO4), filtered, evaporated then dried further under vacuum to give 34 mg of 4-(2,4-dichloro-phenyl)-1H-pyrazole-3-carboxylic acid 4-(4-methyl-piperazin-1-yl)-benzylamide. (LC/MS: Rt 2.42 [M+H]+ 444).

Workup

  1. customThe reaction was evaporated
  2. customthe residue partitioned between ethyl acetate and brine
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthen dried further under vacuum

Sources & evidence

ORD record
ord-9d2f216db55441ec9233b7a07ae0aff9
Source dataset
uspto-grants-2011_12
Patent number
US08080666B2

Reaction notes

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