6-Chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine → 4-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

HRID 873968Notes

Reaction equation

HRID 873968 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.Cl[C:27]1[CH:28]=[C:29]([CH3:37])[C:30]2[N:31]([C:33]([CH3:36])=[N:34][N:35]=2)[N: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]([CH3:37])[C:30]3[N:31]([C:33]([CH3:36])=[N:34][N:35]=3)[N:32]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 155038066-Chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazineHCID 1177026734-(4-chlorophenyl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]-pyrazol-6(1H)-one

Product 1

HCID 862927814-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1-(2-methoxypyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Procedure

The title product was prepared in analogy to the procedure described in Example 110 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 6-chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazine (Step 111.2). The crude material was first purified by silica gel column chromatography (CH2Cl2/MeOH 1-5%), followed by preparative achiral SFC (column Propyl-pyridyl-urea, gradient 9-14% in 6 min_total 11 min). tR: 4.71 min (HPLC 1); tR: 1.10 min (LC-MS 2); ESI-MS: 501 [M+H]+ (LC-MS 2); Rf=0.44 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (s, 3H) 2.51-2.57 (m, 6H) 3.92 (s, 3H) 6.61 (s, 1H) 7.20 (dd, J=7.8, 5.1 Hz, 1H) 7.37-7.44 (m, 2H) 7.47-7.54 (m, 2H) 7.97-8.06 (m, 2H) 8.32 (d, J=4.3 Hz, 1H).

Workup

  1. customThe crude material was first purified by silica gel column chromatography (CH2Cl2/MeOH 1-5%)
  2. customfollowed by preparative achiral SFC (column Propyl-pyridyl-urea, gradient 9-14% in 6 min_total 11 min)

Sources & evidence

ORD record
ord-187c1b628f4d421bb62f5bb65c509f0c
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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