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Hydrochloric Acid → HCID 44539934, Verbindung

HRID 1695795
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695795
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([NH:24][C:25]([C:27]3[N:28]=[C:29]([CH3:32])[S:30][CH:31]=3)=[O:26])[C:12]3[C:16]([CH:17]=2)=[N:15][N:14](C2CCCCO2)[CH:13]=3)[CH:5]=[N:6][C:7]=1[Cl:8].[CH3:33][C:34]1[CH:35]=[CH:36][C:37]([O:44][CH3:45])=[C:38]([S:40](Cl)(=[O:42])=[O:41])[CH:39]=1.Cl>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Cl:8][C:7]1[N:6]=[CH:5][C:4]([C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[C:11]([NH:24][C:25]([C:27]3[N:28]=[C:29]([CH3:32])[S:30][CH:31]=3)=[O:26])[CH:10]=2)=[CH:3][C:2]=1[NH:1][S:40]([C:38]1[CH:39]=[C:34]([CH3:33])[CH:35]=[CH:36][C:37]=1[O:44][CH3:45])(=[O:42])=[O:41]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 1451496-Methoxy-m-toluenesulfonyl chloride3×HCID 58255741N-[6-(5-Amino-6-chloro-3-pyridinyl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Produkt 1

HCID 44539934HCID 44539934, VerbindungAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 1049PyridineLösungsmittel

Versuchsvorschrift

N-[6-(5-Amino-6-chloro-3-pyridinyl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide (50 mg) was dissolved in pyridine (1 ml) and 5-methyl-2-(methyloxy)benzenesulfonyl chloride (35 mg) was added. The reaction was stirred at RT overnight. Further 5-methyl-2-(methyloxy)benzenesulfonyl chloride (35 mg) was added and the reaction was stirred at RT for 4 h. DMAP (3 mg) followed by 5-methyl-2-(methyloxy)benzenesulfonyl chloride (20 mg) was added and the reaction was stirred at RT overnight. The reaction was neutralised with 2M HCl (aq) and extracted into DCM. The DCM was evaporated and the residue was dissolved in DMSO:methanol (1 ml, 8:1, v/v) and purified by MDAP (method E). The desired fraction was evaporated to dryness and methanol (3 ml) and a few drops of 2M HCl (aq) were added and the reaction stirred for 2 h. The reaction was evaporated to dryness to give title compound (39 mg).

Aufarbeitung

  1. stirringthe reaction was stirred at RT for 4 h
  2. additionwas added
  3. stirringthe reaction was stirred at RT overnight
  4. extractionextracted into DCM
  5. customThe DCM was evaporated
  6. dissolutionthe residue was dissolved in DMSO
  7. custommethanol (1 ml, 8:1, v/v) and purified by MDAP (method E)
  8. customThe desired fraction was evaporated to dryness and methanol (3 ml) and a few drops of 2M HCl (aq)
  9. additionwere added
  10. stirringthe reaction stirred for 2 h
  11. customThe reaction was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-81b7af10fbd046d293c36bb2d61f6da6
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163743B2

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