1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → methyl 1-(2-chlorophenyl)-5-(2-(3-(methylsulfonyl)benzoyl) hydrazinecarbonyl)-1H-pyrazole-3-carboxylate

HRID 877438Notes

Reaction equation

HRID 877438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([OH:15])=O)=[CH:11][C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:9]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:41][S:42]([C:45]1[CH:46]=[C:47]([CH:52]=[CH:53][CH:54]=1)[C:48]([NH:50][NH2:51])=[O:49])(=[O:44])=[O:43]>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([NH:51][NH:50][C:48](=[O:49])[C:47]2[CH:52]=[CH:53][CH:54]=[C:45]([S:42]([CH3:41])(=[O:43])=[O:44])[CH:46]=2)=[O:15])=[CH:11][C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:9]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 167825273-(Methylsulfonyl)benzohydrazideHCID 897828401-(2-chlorophenyl)-3-(methoxycarbonyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 89782853methyl 1-(2-chlorophenyl)-5-(2-(3-(methylsulfonyl)benzoyl) hydrazinecarbonyl)-1H-pyrazole-3-carboxylateYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound 7 (500 mg, 1.78 mmol) in DMF (20 mL at 0° C., EDCI (500 mg, 2.6 mmol) was added and stirred for 15 min. HOBt (351 mg, 2.6 mmol) was added to the reaction mixture and after 30 min stirring 3-(methylsulfonyl)benzohydrazide 3 from Example 1 (450 mg, 2.1 mmol) was added. Reaction mixture was allowed to attain room temperature and stirred for over night. Water (100 mL) was added to the reaction mixture and extracted with ethyl acetate (50 mL×4). Combined organic layer was washed with water, brine, dried over sodium sulphate and concentrated. The crude product on column chromatographic purification using 2% methanol in dichloromethane afforded the title compound 8 (452 mg, 52%).

Workup

  1. additionwas added
  2. customReaction mixture
  3. customto attain room temperature
  4. stirringstirred for over night
  5. extractionextracted with ethyl acetate (50 mL×4)
  6. washCombined organic layer was washed with water, brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. customThe crude product on column chromatographic purification

Sources & evidence

ORD record
ord-fd079ba6fbbd4325b58ea61f197b280b
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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