4-Methyloxybenzyl chloride → Tert-butyl (6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)(4-methoxybenzyl)-carbamate

HRID 873985Notes

Reaction equation

HRID 873985 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([N:12]([CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[C:5]2[N:6]([C:8]([CH3:11])=[N:9][N:10]=2)[N:7]=1

Participants

3

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 117714658Tert-butyl (6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)carbamate

Product 1

HCID 117714660Tert-butyl (6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)(4-methoxybenzyl)-carbamate

Procedure

The title compound was prepared in analogy to the procedure described in Step 112.5 using tert-butyl (6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-yl)carbamate (Step 112.4) and 4-methoxybenzylchloride at 80° C. for 1 hr. The crude product was purified by silica gel column chromatography (hexane/EtOAc 10-25%). tR: 5.35 min (HPLC 1); tR: 1.19 min (LC-MS 2); ESI-MS: 404 [M+H]+ (LC-MS 2); Rf=0.74 (hexane/EtOAc 1:1) Step 126.2: tert-butyl (6-(4-(4-chlorophenyl)-1-cyclopropyl-3-methyl-6-oxopyrrolo[3,4-c]pyrazol-5

Workup

  1. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc 10-25%)

Sources & evidence

ORD record
ord-6bd8d2e8f9244f2fb6e8ce81a2a271ce
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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