Pyrrolidine → HCID 66763844, compound

HRID 2368167Notes

Reaction equation

HRID 2368167 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=2)=[CH:6][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:9].[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>O1CCOCC1>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[O:18][CH3:19])[CH2:11][NH:10][C:8]([C:7]1[CH:6]=[C:5]([C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=2)[N:4]=[N:3][C:2]=1[N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:9]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86662436HCID 86662436, compound

Product 1

HCID 66763844HCID 66763844, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-chloro-N-(3,4-dimethoxybenzyl)-6-(3,5-dimethylphenyl)pyridazine-4-carboxamide (1-3, 0.011 g, 0.027 mmol, 1.0 equiv) in dioxane (0.27 mL) was added pyrrolidine (0.038 g, 0.53 mmol, 20.0 equiv) and the reaction mixture was heated to 100° C. under microwave heating for 10 minutes. The reaction was cooled and directly purified by normal phase column chromatography (10 to 100% EtOAc in hexanes) to afford the product (1-4) as a white solid. HRMS [M+H] C26H30N4O3 calc'd 447.2391. found 447.2384.

Workup

  1. temperatureheating for 10 minutes
  2. temperatureThe reaction was cooled
  3. customdirectly purified by normal phase column chromatography (10 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8609444790eb451da326139049f03902
Source dataset
uspto-grants-2014_04
Patent number
US08703770B2

Reaction notes

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