5-iodo-1,3-dimethylpyridin-2(1H)-one → 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873924Notes

Reaction equation

HRID 873924 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]([C:17]4[C:18]([O:23][CH3:24])=[N:19][CH:20]=[CH:21][CH:22]=4)[C:11]=3[C:10](=[O:25])[NH:9]2)=[CH:4][CH:3]=1.I[C:27]1[CH:28]=[C:29]([CH3:35])[C:30](=[O:34])[N:31]([CH3:33])[CH:32]=1>>[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]([C:17]4[C:18]([O:23][CH3:24])=[N:19][CH:20]=[CH:21][CH:22]=4)[C:11]=3[C:10](=[O:25])[N:9]2[C:27]2[CH:28]=[C:29]([CH3:35])[C:30](=[O:34])[N:31]([CH3:33])[CH:32]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 904273665-iodo-1,3-dimethylpyridin-2(1H)-oneHCID 1177026734-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]-pyrazol-6(1H)-one

Product 1

HCID 862923874-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-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 for Example 23 using 4-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 71.4) and 5-iodo-1,3-dimethylpyridin-2(1H)-one (step 23.2) at 100° C. for 16 hr. Further purification by preparative achiral SFC (column Silica, gradient 22-27% in 6 min_total 11 min). tR: 4.34 min (HPLC 1); tR: 1.00 min (LC-MS 2); ESI-MS: 476 [M+H]+ (LC-MS 2); Rf=0.51 (CH2Cl2/MeOH 9:1).

Workup

  1. customFurther purification by preparative achiral SFC (column Silica, gradient 22-27% in 6 min_total 11 min)

Sources & evidence

ORD record
ord-ba1f3c6eb3a7490bbd1957d169f222a5
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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