Trifluoroacetic acid → 2-(7-Amino-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

HRID 33793Notes

Reaction equation

HRID 33793 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:22]3[O:23][C:24]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:25][C:26](=[O:28])[CH:27]=3)[S:11][C:10]=2[CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][CH:21]=1)[S:18][C:17]1[C:16]([C:22]3[O:23][C:24]([N:29]4[CH2:30][CH2:31][O:32][CH2:33][CH2:34]4)=[CH:25][C:26](=[O:28])[CH:27]=3)=[CH:15][CH:14]=[CH:13][C:12]=1[S:11]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59797439[6-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-thianthren-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 597974272-(7-Amino-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [6-(6-morpholin-4-yl-4-oxo-4H-pyran-2-yl)-thianthren-2-yl]-carbamic acid tert-butyl ester (11.95 g, 23.4 mmol) in dichloromethane (150 ml) was added trifluoroacetic acid (30 ml) and left under stirring at room temperature overnight. The solvent was dried in vacuo revealing a viscous dark brown liquid. Saturated sodium bicarbonate solution (400 ml) was added to the residue, which was left to stir for 20 minutes. The brown precipitate was filtered, washing with water and left to dry in a vacuum desiccator overnight. The solid was then purified by column chromatography (silica, MeOH/Dichloromethane, 3:97, Rf=0.28). 1HNMR (300 MHz, CDCl3): δH=3.24 (2H, bs); 3.46 (4H, bs); 3.81 (4H, bs); 6.33 (1H, s); 6.58 (1H, m); 6.86 (1H, d); 7.21 (1H, d); 7.30 (1H, t); 7.38 (1H, d); 7.63 (1H, d); m/z (LC-MS, ESP), RT=3.8 min, (M++1)=411

Workup

  1. waitleft
  2. customThe solvent was dried in vacuo
  3. additionSaturated sodium bicarbonate solution (400 ml) was added to the residue, which
  4. waitwas left
  5. stirringto stir for 20 minutes
  6. filtrationThe brown precipitate was filtered
  7. washwashing with water
  8. waitleft
  9. customto dry in a vacuum desiccator overnight
  10. customThe solid was then purified by column chromatography (silica, MeOH/Dichloromethane, 3:97, Rf=0.28)

Sources & evidence

ORD record
ord-0da2507423fd4bbe88c839ce057f60ce
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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