4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one → tert-butyl (6-(4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-6-oxopyrrolo[3,4-c]pyrazol-5(1H,4H,6H)-yl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)(methyl)carbamate

HRID 873971Notes

Reaction equation

HRID 873971 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][N:12]([CH:17]4[CH2:19][CH2:18]4)[C:11]=3[C:10](=[O:20])[NH:9]2)=[CH:4][CH:3]=1.Cl[C:22]1[CH:23]=[C:24]([N:32]([CH3:40])[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:25]2[N:26]([C:28]([CH3:31])=[N:29][N:30]=2)[N:27]=1>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][N:12]([CH:17]4[CH2:19][CH2:18]4)[C:11]=3[C:10](=[O:20])[N:9]2[C:22]2[CH:23]=[C:24]([N:32]([CH3:40])[C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])[C:25]3[N:26]([C:28]([CH3:31])=[N:29][N:30]=3)[N:27]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1177027334-(4-chlorophenyl)-1-cyclopropyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-oneHCID 117714659Tert-butyl (6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)(methyl)carbamate

Product 1

HCID 86292782tert-butyl (6-(4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-6-oxopyrrolo[3,4-c]pyrazol-5(1H,4H,6H)-yl)-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Example 110 using 4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 85.6) and tert-butyl (6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)(methyl)carbamate (Step 112.5). tR: 5.60 min (HPLC 1); tR: 1.29 min (LC-MS 2); ESI-MS: 549 [M+H]+ (LC-MS 2); Rf=0.56 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.03-1.09 (m, 2H) 1.19-1.25 (m, 2H) 1.43 (s, 9H) 1.90 (s, 3H) 2.52 (s, 3H) 3.44 (s, 3H) 3.79-3.88 (m, 1H) 6.45 (s, 1H) 7.33-7.38 (m, 2H) 7.43-7.48 (m, 2H) 8.30 (s, 1H).

Sources & evidence

ORD record
ord-d46e37ca8e1e4950be0c509945b4fe99
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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