1-[3-(Benzyloxy)phenyl]-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide → 3-[3-(Morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]phenol

HRID 1521837Notes

Reaction equation

HRID 1521837 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([N:15]2[C:19]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[S:26](=[O:29])(=[O:28])[CH2:27][C:18]=3[C:17]([C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:31])=[N:16]2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[N:32]1([C:30]([C:17]2[C:18]3[CH2:27][S:26](=[O:28])(=[O:29])[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:19]=3[N:15]([C:11]3[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=3)[N:16]=2)=[O:31])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

5

Reactant 2

HCID 665789561-[3-(Benzyloxy)phenyl]-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 665789283-[3-(Morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]phenolYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution 1-[3-(benzyloxy)phenyl]-3-(morpholin-4-ylcarbonyl)-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (8 g, 155 mmol) in MeOH (500 mL) is added 10% Pd/C (0.5 g) and the reaction mixture is hydrogenated at 12 Kg/cm2 pressure of hydrogen at RT for 20 h in Autoclave. The catalyst is filtered through celite and filtrate is concentrated to afford 4.9 g (89%) of the title compound as a brown solid. 1H NMR (DMSO-d6, 400 MHz): δ 10.08 (s, 1H), 8.02-8.00 (dd, J=2.4, 3.2 Hz, 1H), 7.65-7.59 (m, 2H), 7.42-7.38 (t, J=8.0 Hz, 1H), 7.01-6.99 (t, J=8.4 Hz, 1H), 6.93-6.88 (m, 3H), 4.88 (s, 2H), 3.95 (m, 2H), 3.66-3.61 (m, 4H), 3.56 (s, 2H). MS (ESI+): 426.0. HPLC (max plot): 96%; Rt 3.25 min.

Workup

  1. filtrationThe catalyst is filtered through celite and filtrate
  2. concentrationis concentrated

Sources & evidence

ORD record
ord-3210555fed894594bfe691aabe6f6b72
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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