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

HRID 873958Notes

Reaction equation

HRID 873958 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[C:32]([O:37][CH3:38])=[N:33][CH:34]=[CH:35][CH:36]=1)[NH2:30]>>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([CH:8]2[C:4]3[C:1]([CH3:2])=[N:30][N:29]([C:31]4[C:32]([O:37][CH3:38])=[N:33][CH:34]=[CH:35][CH:36]=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:14][CH:13]=1

Participants

3

Reactant 2

HCID 445425503-Hydrazinyl-2-methoxypyridineHCID 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 862931604-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-(2-methoxypyridin-3-yl)-3-methyl-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 3-hydrazinyl-2-methoxypyridine (Step 71.1). The crude material was purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2) followed by preparative achiral SFC (column Propyl-pyridyl-urea, gradient 12-17% in 6 min_total 11 min) and triturated in Et2O. tR: 0.99 min (LC-MS 2); ESI-MS: 500 [M+H]+ (LC-MS 2); Rf=0.33 (1% ammonia/5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.07 (s, 3H) 2.45 (s, 3H) 2.62 (s, 3H) 3.92 (s, 3H) 6.59 (s, 1H) 7.21 (dd, J=7.6, 5.01 Hz, 1H) 7.34 (s, 1H) 7.37-7.48 (m, 4H) 8.00 (dd, J=7.6, 1.71 Hz, 1H) 8.33 (dd, J=4.9, 1.6 Hz, 1H) 8.47 (s, 1H).

Workup

  1. customThe crude material was purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2)
  2. customfollowed by preparative achiral SFC (column Propyl-pyridyl-urea, gradient 12-17% in 6 min_total 11 min)
  3. customtriturated in Et2O

Sources & evidence

ORD record
ord-4478ca88804b4b988a6ae6aec32fc16c
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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