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

HRID 857488Notes

Reaction equation

HRID 857488 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 I4d (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%): +APCI 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. customA solid precipitated out of solution
  6. filtrationwas collected by filtration
  7. customto give 3A-1 (11 mg, 38%)

Sources & evidence

ORD record
ord-7d60f00afa49425d8607f6c96b72a566
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

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