Chloroform → (Z)-3-chloro-N-(3-(2-(4-(4-methylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-4-yloxy)phenyl)acrylamide

HRID 1850018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850018
[NH2:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[O:5][C:6]1[C:7]2[S:28][CH:27]=[CH:26][C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[N:11]=1.[Cl:32]/[CH:33]=[CH:34]\[C:35](O)=[O:36].Cl.CN(C)CCCN=C=NCC.C(Cl)(Cl)Cl>N1C=CC=CC=1.CC(O)C>[Cl:32]/[CH:33]=[CH:34]\[C:35]([NH:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:4]([O:5][C:6]2[C:7]3[S:28][CH:27]=[CH:26][C:8]=3[N:9]=[C:10]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]4)=[CH:17][CH:18]=3)[N:11]=2)[CH:3]=1)=[O:36]

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 643794cis-3-Chloroacrylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 895474154-(3-Aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amine

Produkt 1

HCID 86682833(Z)-3-chloro-N-(3-(2-(4-(4-methylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-4-yloxy)phenyl)acrylamideAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

The compound (50 mg, 0.12 mmol) obtained in Step 5 of Example 1 was dissolved in pyridine (1.5 mL), and cis-3-chloroacrylic acid (18 mg, 0.17 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloric acid salt (44 mg, 0.23 mmol) were added thereto, followed by stirring at room temperature for 1 hour. After the reaction was complete, the reaction mixture was dilluted with a mixed solvent (chloroform:2-propanol=3:1 (volume ratio)) and washed with sat. brine. The organic layer was dried with anhydrous sodium sulfate and then filtered and distilled under a reduced pressure. The residue was separated by column chromatography (dichloromethane: methanol=6:1 (volume ratio)) to obtain the title compound (yield: 15 mg, 24%).

Aufarbeitung

  1. washwashed with sat. brine
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. distillationdistilled under a reduced pressure
  5. customThe residue was separated by column chromatography (dichloromethane: methanol=6:1 (volume ratio))

Quellen und Nachweise

ORD-Eintrag
ord-cfe0606cb8b84abb8d02888ae2e3d385
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957065B2

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