5-hydrazinyl-1-methyl-1H-pyrazole → 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

HRID 873947Notes

Reaction equation

HRID 873947 reaction equation
[C:1]([C:4]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:7]([C:16]2[CH:17]=[C:18]([CH3:26])[C:19]3[N:20]([C:22]([CH3:25])=[N:23][N:24]=3)[CH:21]=2)[C:6](=[O:27])[C:5]=1O)(=O)[CH3:2].[NH:29]([C:31]1[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=1)[NH2:30]>>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]2[C:4]3[C:1]([CH3:2])=[N:30][N:29]([C:31]4[N:35]([CH3:36])[N:34]=[CH:33][CH:32]=4)[C:5]=3[C:6](=[O:27])[N:7]2[C:16]2[CH:17]=[C:18]([CH3:26])[C:19]3[N:20]([C:22]([CH3:25])=[N:23][N:24]=3)[CH:21]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 684257025-hydrazinyl-1-methyl-1H-pyrazoleHCID 1177026714-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

Product 1

HCID 862935394-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Procedure

The title compound was prepared in analogy to the procedure described in Example 57 using 4-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one (Step 90.1) and 5-hydrazinyl-1-methyl-1H-pyrazole (Step 74.2). The crude material was purified by silica gel column chromatography (1% ammonia/7.5% MeOH/CH2Cl2) and triturated in Et2O. tR: 0.92 min (LC-MS 2); ESI-MS: 473 [M+H]+ (LC-MS 2); Rf=0.34 (1% ammonia/7.5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.06 (s, 3H) 2.43 (s, 3H) 2.60 (s, 3H) 3.85 (s, 3H) 6.55 (s, 1H) 6.58-6.68 (m, 1H) 7.31 (s, 1H) 7.37 (m, J=8.6 Hz, 2H) 7.45 (m, J=8.6 Hz, 2H) 7.56 (d, J=2.4 Hz, 1H) 8.44 (s, 1H).

Workup

  1. customThe crude material was purified by silica gel column chromatography (1% ammonia/7.5% MeOH/CH2Cl2)
  2. customtriturated in Et2O

Sources & evidence

ORD record
ord-193dc521c98a4408ab4be17727977f3c
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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