Diisopropylethylamine → Selurampanel

HRID 1894077Notes

Reaction equation

HRID 1894077 reaction equation
[CH3:1][S:2]([NH:5][NH2:6])(=[O:4])=[O:3].CCN(C(C)C)C(C)C.C[O:17][C:18](=O)[C:19]1[CH:24]=[C:23]([C:25]2[N:26]([CH3:30])[N:27]=[CH:28][CH:29]=2)[C:22]([CH:31]([CH3:33])[CH3:32])=[CH:21][C:20]=1[NH:34][C:35](OC1C=CC(Cl)=CC=1)=[O:36]>O1CCOCC1>[CH:31]([C:22]1[CH:21]=[C:20]2[C:19]([C:18](=[O:17])[N:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:35](=[O:36])[NH:34]2)=[CH:24][C:23]=1[C:25]1[N:26]([CH3:30])[N:27]=[CH:28][CH:29]=1)([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 269268MethanesulfonohydrazideHCID 59164510HCID 59164510, compound

Product 1

HCID 45381907SelurampanelYield 48.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

CH3SO2NHNH2 (79.5 mg, 1.1 equiv) and i-Pr2NEt (225 μL, 2 equiv) were added to a solution of 2-(4-chloro-phenoxycarbonylamino)-4-isopropyl-5-(2-methyl-2H-pyrazol-3-yl)-benzoic acid methyl ester (281 mg, 0.65 mmol) in dioxane (8 mL). The mixture was stirred for 16 h (TLC control) at 80° C. The mixture was evaporated to dryness. The crude product was purified by flash chromatography (MeOH/DCM (1:9)) to provide N-[7-isopropyl-6-(2-methyl-2H-pyrazol-3-yl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide as a white solid (120 mg, 48%) (ESI-MS: m/z 378 [M+H]+, rt 4.20 min).

Workup

  1. customThe mixture was evaporated to dryness
  2. customThe crude product was purified by flash chromatography (MeOH/DCM (1:9))

Sources & evidence

ORD record
ord-cdee1d25cf15459e9f4ed9b48ba17f8b
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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