tert-butyl 2-(methylsulfanyl)-4,5-dihydro-1H-imidazole-1-carboxylate → 2-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-ylamino]-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester

HRID 1796663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796663
Cl.[NH2:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1.[C:29]([O:33][C:34]([N:36]1[CH2:40][CH2:39][N:38]=[C:37]1SC)=[O:35])([CH3:32])([CH3:31])[CH3:30]>CO.C(Cl)(Cl)Cl>[C:29]([O:33][C:34]([N:36]1[CH2:40][CH2:39][N:38]=[C:37]1[NH:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1)=[O:35])([CH3:32])([CH3:30])[CH3:31]

Komponenten

5

Edukt 2

HCID 15456372tert-butyl 2-(methylsulfanyl)-4,5-dihydro-1H-imidazole-1-carboxylateHCID 221794876-Amino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile hydrochloride

Produkt 1

HCID 210251732-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-ylamino]-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 6-amino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile hydrochloride (Example 11) (49 mg, 0.125 mmol) and 2-methylsulfanyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester (25.5 mg, 0.125 mmol) in MeOH (2 ml) was heated at 70° C. for 3 h, then cooled to rt and stirred overnight. The reaction mixture was diluted with CHCl3 (25 ml), washed with saturated NaHCO3 (10 ml) dried with Na2SO4. Concentrated in vacuo and purified by prep. TLC to give 424A (22 mg, 97%) as pale yellow flakes (5% MeOH—CHCl3). It has a retention time of 6.82 min (standard LC1 method, 8 min run). MS Found: (M+M)+=523.9

Aufarbeitung

  1. temperaturecooled to rt
  2. washwashed with saturated NaHCO3 (10 ml)
  3. dry with materialdried with Na2SO4
  4. concentrationConcentrated in vacuo
  5. custompurified by prep

Quellen und Nachweise

ORD-Eintrag
ord-bd6e779f4dc941cf99d6b271480ec09f
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030112B2

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