Hydrochloric Acid → HCID 67320835, compound

HRID 1875856Notes

Reaction equation

HRID 1875856 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][NH2:24])=[O:22])[C:9]=2[S:25][CH3:26])=[CH:4][CH:3]=1.[C:27](O)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][NH:24][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:22])[C:9]=2[S:25][CH3:26])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6417Pivalic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67321169HCID 67321169, compound

Product 1

HCID 67320835HCID 67320835, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(methylthio)-1H-pyrazole-3-carbohydrazide (7) (200 mg, 0.47 mmol), pivalic acid (8) (57 mg, 0.56 mmol) and EDCI (134 mg, 0.70 mmol) dissolved in CH2Cl2 (30 ml) was added DMAP (114 mg, 0.93 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature for 12 hrs, and then treated with 1N—HCl solution. The organic layer was collected, and evaporated under a vacuum. The crude mixture was further purified by preparative HPLC, to obtain 150 mg (63%) of the title compound as a white solid.

Workup

  1. customThe organic layer was collected
  2. customevaporated under a vacuum
  3. customThe crude mixture was further purified by preparative HPLC

Sources & evidence

ORD record
ord-d7574912761146f1ab84be3a36b0d74d
Source dataset
uspto-grants-2012_11
Patent number
US08309584B2

Reaction notes

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