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

HRID 873953Notes

Reaction equation

HRID 873953 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[CH2:20][CH2:19][CH2:18]4)[C:11]=3[C:10](=[O:21])[NH:9]2)=[CH:4][CH:3]=1.I[C:23]1[CH:24]=[C:25]([CH3:31])[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=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]([CH:17]4[CH2:20][CH2:19][CH2:18]4)[C:11]=3[C:10](=[O:21])[N:9]2[C:23]2[CH:24]=[C:25]([CH3:31])[C:26](=[O:30])[N:27]([CH3:29])[CH:28]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 904273665-iodo-1,3-dimethylpyridin-2(1H)-oneHCID 1177029764-(4-chlorophenyl)-1-cyclobutyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Product 1

HCID 862933524-(4-chlorophenyl)-1-cyclobutyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-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 23 using 4-(4-chlorophenyl)-1-cyclobutyl-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 94.1) and 5-iodo-1,3-dimethylpyridin-2(1H)-one (Step 23.2) 16 hr at 100° C. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 0.5-2%) followed by trituration in hexane/Et2O (3:1). tR: 4.74 min (HPLC 1); tR: 1.08 min (LC-MS 2); ESI-MS: 423 [M+H]+ (LC-MS 2); Rf=0.50 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.84 (m, 2H) 1.90-1.94 (m, 6H) 2.34-2.45 (m, 2H) 2.57-2.73 (m, 2H) 3.35 (s, 3H) 4.91-5.04 (m, 1H) 6.06 (s, 1H) 7.25 (d, J=8.6 Hz, 2H) 7.33-7.40 (m, 3H) 7.72 (d, J=2.7 Hz, 1H).

Workup

  1. customThe crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 0.5-2%)

Sources & evidence

ORD record
ord-1076e324dbdb4b479acd8e0a14595893
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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