HCID 66580952, compound → HCID 66578900, compound

HRID 1521842Notes

Reaction equation

HRID 1521842 reaction equation
[N+:1]([C:4]1[C:5]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)([O-])=O>CCOC(C)=O.[Pd]>[N:17]1([C:15]([C:5]2[C:4]([NH2:1])=[CH:8][N:7]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:6]=2)=[O:16])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

4

Reactant 1

HCID 66580952HCID 66580952, compound

Product 1

HCID 66578900HCID 66578900, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[(4-nitro-1-phenyl-1H-pyrazol-3-yl)carbonyl]morpholine (376 mg; 1.24 mmol; 1.00 eq.) in AcOEt (10 mL) is added Pd/C 10% (-50% H2O) (13.24 mg; 0.12 mmol; 0.10 eq.) and under H2 Atm. (1 atm.). After 18 h, reaction mixture is filtered over a celite bed, ished with AcOEt to give 310 mg (92%) of the title compound as a purple solid. 1H NMR (DMSO): δ 7.85 (s, 1H), 7.77-7.72 (m, 2H), 7.53-7.44 (m, 2H), 7.30 (t, J=7.4 Hz, 1H), 5.14-4.90 (m, 2H), 4.31-4.14 (m, 2H), 3.73-3.58 (m, 4H), 3.43-3.23 (m, 2H). HPLC (max plot) 95.6%; Rt 2.01 min. MS (ESI+): 272.9.

Workup

  1. customreaction mixture
  2. filtrationis filtered over a celite bed

Sources & evidence

ORD record
ord-340e85eb4d92471599592f7a201940be
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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