1,2-Dichloro-3-isocyanatobenzene → 1-(5-tert-butyl-3-(2,2-dimethyl-3-oxopiperazine-1-carbonyl)-1H-pyrrol-2-yl)-3-(2,3-dichlorophenyl)urea

HRID 18938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18938
[NH2:1][C:2]1[NH:3][C:4]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:5][C:6]=1[C:7]([N:9]1[CH2:14][CH2:13][NH:12][C:11](=[O:15])[C:10]1([CH3:17])[CH3:16])=[O:8].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]=[C:30]=[O:31])[C:24]=1[Cl:32]>C1COCC1>[C:18]([C:4]1[NH:3][C:2]([NH:1][C:30]([NH:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[C:24]=2[Cl:32])=[O:31])=[C:6]([C:7]([N:9]2[CH2:14][CH2:13][NH:12][C:11](=[O:15])[C:10]2([CH3:16])[CH3:17])=[O:8])[CH:5]=1)([CH3:21])([CH3:20])[CH3:19]

Komponenten

4

Edukt 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 586792354-(2-amino-5-tert-butyl-1H-pyrrole-3-carbonyl)-3,3-dimethylpiperazin-2-one

Produkt 1

HCID 586791571-(5-tert-butyl-3-(2,2-dimethyl-3-oxopiperazine-1-carbonyl)-1H-pyrrol-2-yl)-3-(2,3-dichlorophenyl)ureaAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 4-(2-amino-5-tert-butyl-1H-pyrrole-3-carbonyl)-3,3-dimethyl-piperazin-2-one 7 (60 mg, 0.21 mmol) in THF (1 mL) was added 1,2-dichloro-3-isocyanatobenzene (58 mg, 0.31 mmol) in THF (1 mL). The resulting reaction mixture was stirred at room temperature for 1 h, at which time, TLC indicated the completion of the reaction. The solvent was then removed in vacuo, and the residue was purified by prep. TLC (EtOAc/MeOH: 9.5/0.5) to provide 1-(5-tert-butyl-3-(2,2-dimethyl-3-oxopiperazine-1-carbonyl)-1H-pyrrol-2-yl)-3-(2,3-dichlorophenyl)urea (14.6 mg, 15%) as off-white solid. 1H NMR (400 MHz, CD3OD): δ (ppm) 7.93 (t, J=4.9 Hz, 1H), 7.20 (q, J=1.9 Hz, 2H), 5.68 (s, 1H), 3.87 (t, J=5.1 Hz, 2H), 3.44 (t, J=5.0 Hz, 2H), 1.75 (s, 6H), 1.25 (s, 9H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customthe completion of the reaction
  3. customThe solvent was then removed in vacuo
  4. customthe residue was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-974a177645f54e899abbc1a755582b13
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741479B2

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