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

HRID 1618725Notes

Reaction equation

HRID 1618725 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b6c3ea7cfc7d45f3904a0fcdf1b595b7
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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