Hydrochloric Acid → 4-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-indazol-3-amine

HRID 1909925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909925
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[N:4]([CH3:27])[N:3]=1.Cl>CCO>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[C:2]([NH2:1])=[N:3][N:4]4[CH3:27])=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 668240801,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate

Produkt 1

HCID 668237234-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-indazol-3-amineAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a stirred suspension of 1,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate (1.70 g, 4.66 mmol) in 20 mL of EtOH was added 12 mL of 2N HCl. The mixture was heated at 75° C. for 90 min. LCMS showed conversion complete. The mixture was cooled, and concentrated in vacuo. The oily residue was diluted with 40 mL of water, and the pH was adjusted to ˜10 by adding 1N NaOH (pH paper). The milky mixture was extracted with 10° A MeOH in DCM (100 mL, then 2×25 mL). The combined organic was dried over Na2SO4, filtered, and concentrated in vacuo to give 4-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-indazol-3-amine as a brownish foamy solid (1.13 g). LC-MS (ES) m/z=265 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionThe oily residue was diluted with 40 mL of water
  4. additionby adding 1N NaOH (pH paper)
  5. extractionThe milky mixture was extracted with 10° A MeOH in DCM (100 mL
  6. dry with materialThe combined organic was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-779ac28084634a5fb1ab05999f1487ae
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598156B2

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