5-Chloro-3,7-dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridine → 4-(4-chlorophenyl)-5-(3,7-dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridin-5-yl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873964Notes

Reaction equation

HRID 873964 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[N:10][C:5]2=[C:4]([CH3:12])[CH:3]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[C:27]3[C:26]([CH3:28])=[N:25][N:24]([C:29]4[C:30]([O:35][CH3:36])=[N:31][CH:32]=[CH:33][CH:34]=4)[C:23]=3[C:22](=[O:37])[NH:21]2)=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[C:27]3[C:26]([CH3:28])=[N:25][N:24]([C:29]4[C:30]([O:35][CH3:36])=[N:31][CH:32]=[CH:33][CH:34]=4)[C:23]=3[C:22](=[O:37])[N:21]2[C:2]2[N:7]=[C:6]3[N:8]([CH3:11])[N:9]=[N:10][C:5]3=[C:4]([CH3:12])[CH:3]=2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 1177026225-Chloro-3,7-dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridineHCID 1177026734-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]-pyrazol-6(1H)-one

Product 1

HCID 862929694-(4-chlorophenyl)-5-(3,7-dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridin-5-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 102 using 5-chloro-3,7-dimethyl-3H-[1,2,3]triazolo[4,5-b]pyridine (Step 109.4) and 4-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 71.4). The crude material was first purified by silica gel chromatography (40% EtOAc/Hexane) followed by preparative achiral SFC (column 4-Ethyl-pyridine, gradient 6-11% in 6 min_total 11 min). tR: 1.25 min (LC-MS 2); ESI-MS: 501 [M+H]+ (LC-MS 2); Rf=0.19 (40% EtOAc/hexane); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.04 (s, 3H) 2.66 (s, 3H) 3.92 (s, 3H) 4.10 (s, 3H) 6.74 (s, 1H) 7.14-7.26 (m, 1H) 7.36 (m, J=8.6 Hz, 2H) 7.49 (m, J=8.6 Hz, 2H) 7.96-8.05 (m, 1H) 8.14 (d, J=0.8 Hz, 1H) 8.28-8.38 (m, 1H).

Workup

  1. customThe crude material was first purified by silica gel chromatography (40% EtOAc/Hexane)
  2. customfollowed by preparative achiral SFC (column 4-Ethyl-pyridine, gradient 6-11% in 6 min_total 11 min)

Sources & evidence

ORD record
ord-4c55664ca56d4701bb761300149266cf
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…