Trifluoroacetic acid → 4-(2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazin-7-yl)morpholine

HRID 1618725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618725
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:23]=[N:22][C:10]3[S:11][CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[C:9]=3[CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:14]1[CH2:13][CH2:12][S:11][C:10]2[N:22]=[CH:23][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:8][C:9]1=2

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67284534tert-butyl 7-morpholino-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-1-carboxylate

Produkt 1

HCID 672845584-(2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazin-7-yl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl 7-morpholino-2,3-dihydro-1H-pyrido[2,3-b]-[1,4]thiazine-1-carboxylate (280 mg, 0.83 mmol) in DCM (2.0 mL) was added TFA (3.2 mL, 41.5 mmol). The reaction was stirred at rt for 2 h and evaporated in vacuo. The resulting residue was dissolved in DCM (40 mL) and washed with NaHCO3 (20 mL, saturated aqueous solution). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo to give 4-(2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazin-7-yl)morpholine as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.62 (1H, d, J=2.5 Hz), 6.26 (1H, d, J=2.5 Hz), 3.82-3.87 (4H, m), 3.59-3.63 (2H, m), 3.13-3.17 (2H, m), 3.06-3.10 (4H, m). Mass Spectrum (ESI) m/e=238.2 (M+1).

Aufarbeitung

  1. customevaporated in vacuo
  2. dissolutionThe resulting residue was dissolved in DCM (40 mL)
  3. washwashed with NaHCO3 (20 mL, saturated aqueous solution)
  4. dry with materialThe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6c3ea7cfc7d45f3904a0fcdf1b595b7
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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