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

HRID 2170583Notes

Reaction equation

HRID 2170583 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-9ff44700124b4addbb4d4f06658a4d6d
Source dataset
uspto-grants-2015_06
Patent number
US09051278B2

Reaction notes

Loading…