Hydrochloric Acid → Tert-butyl 5-amino-2-chloropyridin-3-ylcarbamate

HRID 1622011

Reaktionsgleichung

Reaktionsgleichung von HRID 1622011
[Cl:1][C:2]1[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:5]([N:16]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][N:3]=1.Cl>C1COCC1>[NH2:16][C:5]1[CH:6]=[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[C:2]([Cl:1])=[N:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86647087Tert-butyl 2-chloro-5-(diphenylmethyleneamino)pyridin-3-ylcarbamate

Produkt 1

HCID 86647086Tert-butyl 5-amino-2-chloropyridin-3-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-chloro-5-(diphenylmethyleneamino)pyridin-3-ylcarbamate (0.280 g, 0.686 mmol) in THF (5 mL) was added hydrochloric acid, In (JT Baker) (0.031 mL, 1.030 mmol). The reaction was stirred at rt in closed system for 20 min. The reaction mixture was partitioned between EtOAc/sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (24 g, 3% MeOH in DCM) to afford the desired product as a white foam-like solid (135.0 mg). MS (ESI pos. ion) m/z: 244.1. 1H NMR (300 MHz, CDCl3) δ ppm 1.54 (s, 9H) 3.73 (br. s., 2H) 6.93 (br. s., 1H) 7.52 (d, J=2.63 Hz, 1H) 7.94 (d, J=2.63 Hz, 1H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc/
  2. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layer were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (24 g, 3% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-8bd3a173dbf941afa14831e974a6f03c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772480B2

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