Hydrochloric Acid → HCID 24764798, Verbindung

HRID 911795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911795
[Br:1][C:2]1[CH:3]=[C:4]([O:15][CH:16]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.C(Cl)[Cl:29].CO.[ClH:33]>O1CCOCC1>[ClH:29].[ClH:33].[Br:1][C:2]1[CH:3]=[C:4]([O:15][CH:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6344DichloromethaneHCID 24764797Tert-butyl 3-(5-bromo-2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)pyrrolidine-1-carboxylate

Produkt 1

HCID 24764798HCID 24764798, VerbindungAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 3-(5-bromo-2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)pyrrolidine-1-carboxylate (prepared according to Example 61; 550 mg, 1.21 mmol) and CH2Cl2 (10 mL) and MeOH (2 mL) was stirred at room temperature. 4N HCl in dioxane (5 mL) was added and the reaction mixture was stirred at room temperature for 30 minutes. The reaction was concentrated and dissolved in small amount of CH2Cl2/methanol and added to vigorously stirred ether and filtered to afford N-(5-bromo-3-(pyrrolidin-3-yloxy)pyridin-2-yl)-4-methylthiazol-2-amine dihydrochloride (478 mg, 92.4% yield) as a white solid. 1H NMR (d6-DMSO) δ 11.18 (bs, 1H), 9.80 (bs, 1H), 9.27 (bs, 1H), 8.09 (d, 1H), 7.83 (d, 1H), 6.80 (s, 1H), 5.42 (m, 1H), 3.62-3.30 (m, 4H), 2.31 (s, 3H), 2.22 (m, 2H); Mass spectrum (apci) m/z 357.0 (M+H-2HCl).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved in small amount of CH2Cl2/methanol
  4. additionadded to vigorously stirred ether
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-3e60c6f0bd3f4fc09e75bbfd2307a2da
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022223B2

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