5-hydrazinyl-1-methyl-1H-pyrazole → 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-ethyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873946Notes

Reaction equation

HRID 873946 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]([C:13](=O)[CH2:14][CH3:15])=[C:11](O)[C:10](=[O:18])[N:9]2[C:19]2[CH:20]=[C:21]([CH3:27])[C:22](=[O:26])[N:23]([CH3:25])[CH:24]=2)=[CH:4][CH:3]=1.[NH:28]([C:30]1[N:34]([CH3:35])[N:33]=[CH:32][CH:31]=1)[NH2:29]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]3[C:13]([CH2:14][CH3:15])=[N:29][N:28]([C:30]4[N:34]([CH3:35])[N:33]=[CH:32][CH:31]=4)[C:11]=3[C:10](=[O:18])[N:9]2[C:19]2[CH:20]=[C:21]([CH3:27])[C:22](=[O:26])[N:23]([CH3:25])[CH:24]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 684257025-hydrazinyl-1-methyl-1H-pyrazoleHCID 1177027685-(2-(4-chlorophenyl)-4-hydroxy-5-oxo-3-propionyl-2,5-dihydro-1H-pyrrol-1-yl)-1,3-dimethylpyridin-2(1H)-one

Product 1

HCID 862935384-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-ethyl-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 5-(2-(4-chlorophenyl)-4-hydroxy-5-oxo-3-propionyl-2,5-dihydro-1H-pyrrol-1-yl)-1,3-dimethylpyridin-2(1H)-one (Step 89.1) and 5-hydrazinyl-1-methyl-1H-pyrazole (Step 74.2). The crude material was first purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2) followed by preparative achiral SFC (column 4-Ethyl-pyridine, gradient 10-15% in 6 min_total 11 min) and trituration in Et2O. tR: 1.01 min (LC-MS 2); ESI-MS: 463 [M+H]+ (LC-MS 2); Rf=0.42 (1% ammonia/5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97 (t, J=7.6 Hz, 3H) 1.94 (s, 3H) 2.35-2.48 (m, 2H) 3.37 (s, 3H) 3.86 (s, 3H) 6.25 (s, 1H) 6.63 (d, J=2.0 Hz, 1H) 7.34-7.48 (m, 5H) 7.58 (d, J=1.9 Hz, 1H) 7.75 (d, J=2.4 Hz, 1H).

Workup

  1. customThe crude material was first purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2)
  2. customfollowed by preparative achiral SFC (column 4-Ethyl-pyridine, gradient 10-15% in 6 min_total 11 min) and trituration in Et2O

Sources & evidence

ORD record
ord-4dad390cb33249c0a120b0a1bbfae7b7
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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