1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(1-(2-chlorophenyl)-5-(4-chlorophenyl)-3-(4-phenylpiperazine-1-carbonyl)-1H-pyrazol-4-yl)acetonitrile

HRID 1685397Notes

Reaction equation

HRID 1685397 reaction equation
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:22]=[C:21]([C:31]([OH:33])=O)[C:20]=2[CH2:34][C:35]#[N:36])=[CH:15][CH:14]=1.[CH:37]1[CH:38]=[CH:39][C:40]2N(O)N=[N:43][C:41]=2[CH:42]=1.[N:47]1(C2N=CC=CN=2)[CH2:52][CH2:51]N[CH2:49][CH2:48]1>ClCCl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:22]=[C:21]([C:31]([N:47]3[CH2:52][CH2:51][N:43]([C:41]4[CH:42]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:49][CH2:48]3)=[O:33])[C:20]=2[CH2:34][C:35]#[N:36])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 887471-(2-Pyrimidinyl)piperazineHCID 591463351-(2-chlorophenyl)-5-(4-chlorophenyl)-4-(cyanomethyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 462251082-(1-(2-chlorophenyl)-5-(4-chlorophenyl)-3-(4-phenylpiperazine-1-carbonyl)-1H-pyrazol-4-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDAC (195 mg, 1.00 mmol) was added to a stirred solution of [B1] (250 mg, 0.7 mmol) and HOBT (133 mg, 0.8 mmol) in dichloromethane (40 ml) at room temperature under argon. After 15 minutes 2-(piperazinyl)pyrimidine (155 mg, 0.9 mmol) was added and stirring continued for 16 hours. The mixture was washed with saturated aqueous sodium bicarbonate solution (3×) then with brine, dried over magnesium sulphate, filtered and evaporated in vacuo to give the crude, which was purified by preparative chromatography to give 9 mg of [C1].

Workup

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate solution (3×)
  2. dry with materialwith brine, dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give the crude, which
  6. customwas purified by preparative chromatography

Sources & evidence

ORD record
ord-e4f56a6fd02a48f4a91a53aa3acf2c4f
Source dataset
uspto-grants-2012_04
Patent number
US08148404B2

Reaction notes

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