Trifluoroacetic acid → HCID 52950520, compound

HRID 1521863Notes

Reaction equation

HRID 1521863 reaction equation
[N:1]1([C:7]([C:9]2[C:10]3[CH2:35][S:34](=[O:37])(=[O:36])[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:11]=3[N:12]([CH2:14][CH:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1([C:7]([C:9]2[C:10]3[CH2:35][S:34](=[O:37])(=[O:36])[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:11]=3[N:12]([CH2:14][CH:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 52950478HCID 52950478, compound

Product 1

HCID 52950520HCID 52950520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-{[3-(morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]methyl}piperidine-1-carboxylate (0.1 g, 0.21 mmol) in DCM (2.0 mL) is added TFA (0.119 g, 1.05 mmol, 5 Eq) and the reaction mixture is stirred at room temperature overnight. The crude reaction mixture is washed with sodium bicarbonate then brine and dried over MgSO4. The crude residue is purified by flash chromatography to afford the title compound as a pale brown solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.03-7.98 (m, 2H), 7.88 (t, J=7.5 Hz, 1H), 7.73-7.70 (m, 1H), 4.78 (s, 2H), 4.47 (t, J=7.1 Hz, 2H), 3.91 (s, 2H), 3.66-3.63 (m, 6H), 2.98-2.95 (m, 2H), 2.00 (brs, 1H), 1.75-1.69 (m, 1H), 1.48-1.40 (m, 2H), 1.24-1.17 (m, 3H). MS (ESI+): 431.0. HPLC (max plot) 97.2%; Rt 2.16 min.

Workup

  1. customThe crude reaction mixture
  2. washis washed with sodium bicarbonate
  3. dry with materialbrine and dried over MgSO4
  4. customThe crude residue is purified by flash chromatography

Sources & evidence

ORD record
ord-1db657e96376435f89cb123b97f60021
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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