Trifluoroacetic acid → 2-(7-Amino-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one

HRID 33808Notes

Reaction equation

HRID 33808 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)[CH2:11][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]([S:18][C:17]3[C:16]([C:22]4[O:23][C:24]([N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[CH:25][C:26](=[O:28])[CH:27]=4)=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23574574[5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 221394022-(7-Amino-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yl]-carbamic acid tert-butyl ester (19) (1.08 g, 2.19 mmol) in dichloromethane (10 ml) was added trifluoroacetic acid (2 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 (20 ml) was added to the residue, which was left to stir for 20 mins. The brown precipitate was filtered, washing with water and left to dry in the vacuum oven overnight (0.77 g, 90%). 1HNMR (300 MHz, DMSO-d6): δH=3.40 (4H, t), 3.70 (4H, t), 3.77 (2H, s), 5.23 (2H, bs), 5.50 (1H, d), 6.17 (1H, d), 6.44 (1H, dd), 6.65 (1H, d), 7.09 (1H, d), 7.35 (1H, t), 7.47-7.59 (2H, m); m/z (LC-MS, ESP), RT=3.51 minutes, (M++1)=392.

Workup

  1. waitleft
  2. customThe solvent was dried in vacuo
  3. additionSaturated sodium bicarbonate solution (20 ml) was added to the residue, which
  4. waitwas left
  5. stirringto stir for 20 mins
  6. filtrationThe brown precipitate was filtered
  7. washwashing with water
  8. waitleft
  9. customto dry in the vacuum oven overnight (0.77 g, 90%)

Sources & evidence

ORD record
ord-68c5968196104529a711a1a1771ea7e6
Source dataset
uspto-grants-2008_09
Patent number
US07429660B2

Reaction notes

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