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

HRID 873995Notes

Reaction equation

HRID 873995 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH2:16][O:17][CH3:18])=[N:13][N:12]([CH:19]4[CH2:21][CH2:20]4)[C:11]=3[C:10](=[O:22])[NH:9]2)=[CH:4][CH:3]=1.Br[C:24]1[CH:25]=[C:26]([CH3:32])[C:27](=[O:31])[N:28]([CH3:30])[CH:29]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH2:16][O:17][CH3:18])=[N:13][N:12]([CH:19]4[CH2:20][CH2:21]4)[C:11]=3[C:10](=[O:22])[N:9]2[C:24]2[CH:25]=[C:26]([CH3:32])[C:27](=[O:31])[N:28]([CH3:30])[CH:29]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 122726645-Bromo-1,3-dimethylpyridin-2(1H)-oneHCID 1177027014-(4-chlorophenyl)-1-cyclopropyl-3-(methoxymethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Product 1

HCID 918263334-(4-chlorophenyl)-1-cyclopropyl-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(methoxymethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Procedure

The title compound was prepared using an analogous procedure to that described in Example but using 4-(4-chlorophenyl)-1-cyclopropyl-3-(methoxymethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 130.4) and 5-bromo-1,3-dimethyl-2-pyridone. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 0.5-3.5%) to provide the title compound (286 mg) as a colorless solid. tR: 0.95 min (LC-MS 2); ESI-MS: 439.1 [M+H]+ (LC-MS 2); Rf=0.48 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00-1.07 (m, 2H) 1.20-1.27 (m, 2H) 1.91 (s, 3H) 3.02 (s, 3H) 3.34 (s, 3H) 3.81-3.89 (m, 1H) 3.97 (d, J=12.51 Hz, 1H) 4.20 (d, J=12.51 Hz, 1H) 6.09 (s, 1H) 7.20-7.28 (m, 2H) 7.31-7.37 (m, 2H) 7.40-7.45 (m, 1H) 7.76 (d, J=2.74 Hz, 1H).

Workup

  1. customThe title compound was prepared
  2. customThe crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 0.5-3.5%)

Sources & evidence

ORD record
ord-6025bbe024ef477cbb791eb053da72ed
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…