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)-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873977Notes

Reaction equation

HRID 873977 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[N:21]([CH3:22])[N:20]=[CH:19][CH:18]=4)[C:11]=3[C:10](=[O:23])[NH:9]2)=[CH:4][CH:3]=1.Cl[C:25]1[CH:26]=[C:27]([CH3:35])[C:28]2[N:29]([C:31]([CH3:34])=[N:32][N:33]=2)[N:30]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][N:12]([C:17]4[N:21]([CH3:22])[N:20]=[CH:19][CH:18]=4)[C:11]=3[C:10](=[O:23])[N:9]2[C:25]2[CH:26]=[C:27]([CH3:35])[C:28]3[N:29]([C:31]([CH3:34])=[N:32][N:33]=3)[N:30]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 155038066-Chloro-3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazineHCID 1177029454-(4-chlorophenyl)-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

Product 1

HCID 862927834-(4-chlorophenyl)-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

Procedure

The title compound was prepared in analogy to the procedure described in Example 110 using 4-(4-chlorophenyl)-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 114.2) 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 NH2, gradient 9-14% in 6 min_total 11 min) and trituration in Et2O. tR: 4.37 min (HPLC 1); tR: 1.01 min (LC-MS 2); ESI-MS: 474 [M+H]+ (LC-MS 2); ESI-MS: 472 [M−H]− (LC-MS 2); Rf=0.45 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.05 (s, 3H) 2.53 (s, 3H) 2.56 (s, 3H) 3.85 (s, 3H) 6.60 (s, 1H) 6.65 (d, J=2.0 Hz, 1H) 7.39 (d, J=8.2 Hz, 2H) 7.54-7.60 (m, 3H) 8.02-8.05 (m, 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 NH2, gradient 9-14% in 6 min_total 11 min) and trituration in Et2O

Sources & evidence

ORD record
ord-15fea066d7004ae0b44744ac6918a5a7
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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