1,2-Dichloroethane → 3-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one

HRID 1766424Notes

Reaction equation

HRID 1766424 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]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:11]([CH2:20][NH:21][CH:22]([CH3:24])[CH3:23])[C:10]([C:25]([OH:27])=O)=[N:9]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]2[N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[N:9]=[C:10]3[C:25](=[O:27])[N:21]([CH:22]([CH3:23])[CH3:24])[CH2:20][C:11]=23)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 218687991-(2-Chloro-phenyl)-5-(4-chloro-phenyl)-4-(isopropylamino-methyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 218687853-(4-chloro-phenyl)-2-(2-chloro-phenyl)-5-isopropyl4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-4-(isopropylamino-methyl)-1H-pyrazole-3-carboxylic acid I-4d (40 mg, 0.074 mmol), EDC (28 mg, 0.148 mmol), HOAt (20 mg, 0.148 mmol), and triethylamine (0.02 ml, 0.148 mmol) in CH2Cl2 (10 ml) was stirred at room temperature for 17 hours. The reaction mixture was washed with sat'd aq NaHCO3, sat'd aq NaCl, dried and concentrated in vacuo. The crude residue was diluted with cyclohexane and stirred for 17 hours. A solid precipitated out of solution and was collected by filtration to give 3A-1 (11 mg, 38%): +APCl MS (M+1) 386.1; 1H NMR (CDCl3) δ 7.50-7.38 (m, 4H), 7.26 (d, 2H, J=9.6 Hz), 7.06 (d, 2H), 4.69 (m, 1H), 1.3 (d, 6H, J=6.65 Hz).

Workup

  1. washThe reaction mixture was washed with sat'd aq NaHCO3
  2. customdried
  3. concentrationconcentrated in vacuo
  4. additionThe crude residue was diluted with cyclohexane
  5. stirringstirred for 17 hours
  6. customA solid precipitated out of solution
  7. filtrationwas collected by filtration
  8. customto give 3A-1 (11 mg, 38%)

Sources & evidence

ORD record
ord-dced26995402483cb3b313849ea3882a
Source dataset
uspto-grants-2007_06
Patent number
US07230024B2

Reaction notes

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