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Acetic Acid → HCID 68467418, Verbindung

HRID 506176
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 506176
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]3[CH:12]=[N:13][CH:14]=[C:15]([C:18]=3[NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[C:16]#[N:17])=[CH:8][C:7]=2[CH:29]=1)=O.[CH3:30][NH:31][CH3:32].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[CH3:30][N:31]([CH2:1][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]3[CH:12]=[N:13][CH:14]=[C:15]([C:18]=3[NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[C:16]#[N:17])=[CH:8][C:7]=2[CH:29]=1)[CH3:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 674Dimethylamine2×HCID 5049666Sodium triacetoxyborohydrideHCID 86616831HCID 86616831, Verbindung

Produkt 1

HCID 68467418HCID 68467418, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To 5-(5-formyl-1-benzothien-2-yl)-4-(1H-indol-4-ylamino)nicotinonitrile 223 (166 mg, 0.38 mmol) in THF (7 mL) was added dimethylamine in THF (2.0 M, 0.58 mL, 1.15 mmol) followed by acetic acid (126 mg, 2.09 mmol). The resulting mixture was stirred at r.t. for 1 h and additional dimethylamine (1.2 mL, 2.30 mmol) was added. After stirring at r.t. for an additional hour, Na(OAc)3BH (242 mg, 1.15 mmol) was added. The reaction mixture was stirred at r.t. for 2 h and was partitioned between diluted HCl and EtOAc. The combined aqueous extracts were basified with aqueous NaHCO3 and extracted with EtOAc. The combined organics were dried over Na2SO4, concentrated and purified by flash column chromatography to give 115 mg (65%) of 5-{5-[(dimethylamino)methyl]-1-benzothien-2-yl}-4-(1H-indol-4-ylamino)nicotinonitrile 224 as a pale yellow solid. MS: 424.2 (M+H); HPLC retention time: 2.1 min.(a).

Aufarbeitung

  1. stirringAfter stirring at r.t. for an additional hour
  2. stirringThe reaction mixture was stirred at r.t. for 2 h
  3. customwas partitioned between diluted HCl and EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1f4f9017616b4df89f1f433e248de6fd
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781591B2

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