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Ethanol → HCID 68209970, Verbindung

HRID 873389
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 873389
C(C1[CH:4]=[C:5]([C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:30])[NH:22][C:23]([CH3:29])=[CH:24][C:25]=2[CH2:26][CH2:27][CH3:28])=[O:17])[C:6]2[C:7]([CH3:15])=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1)#N.[OH-].[K+].C(O)C.CC[O:38][C:39]([CH3:41])=[O:40]>>[CH3:15][C:7]1[C:6]2[C:10](=[CH:11][C:41]([C:39]([OH:38])=[O:40])=[CH:4][C:5]=2[C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:30])[NH:22][C:23]([CH3:29])=[CH:24][C:25]=2[CH2:26][CH2:27][CH3:28])=[O:17])[N:9]([CH:12]([CH3:13])[CH3:14])[CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 546707286-cyano-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indole-4-carboxamide

Produkt 1

HCID 68209970HCID 68209970, VerbindungAusbeute 64,9 %

Versuchsvorschrift

To a 5 ml microwave vial was added, 6-cyano-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indole-4-carboxamide (100 mg, 0.247 mmol), KOH (41.6 mg, 0.742 mmol) was ground and added followed by Ethanol (8 mL) the reaction was microwaved at 145° C. for 22 hr. The reaction was poured onto acidic Ice water (20 mL) and was stirred for 20 min. EtOAc was added and the mix was stirred an additional 10 min. The layers were separated and the majority of the product was in the EtOAc which was evaporated. The residue was dissolved in MeOH (1 mL) and material was crashed out with ice and was filtered to give product 3-methyl-1-(1-methylethyl)-4-({[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]amino}carbonyl)-1H-indole-6-carboxylic acid (70 mg, 0.160 mmol, 64.9% yield) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.49 (br. s., 1 H) 8.18 (s, 1 H) 8.10 (s, 1 H) 7.53 (d, J=7.58 Hz, 2 H) 5.90 (s, 1 H) 4.76-4.90 (m, 1 H) 4.36 (d, J=4.80 Hz, 2 H) 2.55 (br. s., 1 H) 2.18 (s, 3 H) 2.13 (s, 3 H) 1.52-1.61 (m, 2 H) 1.44 (d, J=6.57 Hz, 6 H) 0.94 (t, J=7.33 Hz, 3 H) MS(ES) [M+H]+423.8

Aufarbeitung

  1. additionTo a 5 ml microwave vial was added
  2. additionadded
  3. customwas microwaved at 145° C. for 22 hr
  4. stirringthe mix was stirred an additional 10 min
  5. customThe layers were separated
  6. customwas evaporated
  7. dissolutionThe residue was dissolved in MeOH (1 mL)
  8. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-efd7343aab8c455399604a5fc5e27611
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975291B2

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