Ethanol → tert-butyl N-[4-[3-(3-amino-5-methyl-4-pyridinyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216063

Reaktionsgleichung

Reaktionsgleichung von HRID 2216063
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH3:15])[C:13]=1I)(C)(C)C.[C:17]([O:21][C:22](=[O:45])[NH:23][C:24]([C:26]1[S:27][C:28]([S:43][CH3:44])=[C:29]([S:31]([C:34]2[CH:39]=[CH:38][C:37](O)=[C:36](B)[C:35]=2O)(=[O:33])=[O:32])[CH:30]=1)=[NH:25])([CH3:20])([CH3:19])[CH3:18].C(O)C.C1(C)C=CC=CC=1>C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[C:17]([O:21][C:22](=[O:45])[NH:23][C:24]([C:26]1[S:27][C:28]([S:43][CH3:44])=[C:29]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:13]3[C:12]([CH3:15])=[CH:11][N:10]=[CH:9][C:8]=3[NH2:7])[CH:35]=2)(=[O:33])=[O:32])[CH:30]=1)=[NH:25])([CH3:20])([CH3:19])[CH3:18]

Komponenten

8

Edukt 4

HCID 702EthanolHCID 1140TolueneHCID 60026355(4-Iodo-5-methyl-pyridin-3-yl)-carbamic acid tert-butyl esterHCID 178419158HCID 178419158, Verbindung

Produkt 1

HCID 145857697tert-butyl N-[4-[3-(3-amino-5-methyl-4-pyridinyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

(4-Iodo-5-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester (106 mg, 0.32 mmol, Example 139: step b), {[4-(3-Boranyl-dihydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (145 mg, 0.32 mmol, Example 140: step a) and Pd(PPh3)4 (74 mg, 0.06 mmol) were combined in aqueous Na2CO3 (2M, 1.2 mL), ethanol (1.2 mL) and toluene (2.4 mL) and was heated to 80° C. overnight. The reaction mixture was dissolved into EtOAc and washed with brine. The organic layers were dried (MgSO4) and solvents were removed in vacuo. Purification by flash column chromatography (40% EtOAc/hexanes) afforded the title compound. ESI-MS (m/z): Calcd. for C28H34N4O6S3: 619.2 (M+1); found: 618.8.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialThe organic layers were dried (MgSO4) and solvents
  3. customwere removed in vacuo
  4. customPurification by flash column chromatography (40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bdac16c0a6e84c5b98a1a9d6d963f622
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109354B2

Verknüpfte Notizen

Wird geladen…