Morpholine → HCID 178499639, compound

HRID 1471437Notes

Reaction equation

HRID 1471437 reaction equation
[CH2:1]([NH:8]/[C:9](=[C:12]1/[C:13]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[N:14][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:16]/1=[O:17])/[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:1]([NH:8]/[C:9](=[C:12]1/[C:13]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[N:14][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:16]/1=[O:17])/[CH2:10][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8083Morpholine2×HCID 81531DiisopropylethylamineHCID 178499638HCID 178499638, compound

Product 1

HCID 178499639HCID 178499639, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of the above obtained methyl [(4Z)-4-[1-(benzylamino)-2-chloroethylidene]-1-(2-chlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (XIII), 0.32 g), morpholine (1 eq.) and DIPEA (1 eq.) was stirred at room temperature in toluene (3 mL) under nitrogen for 0.5 h at 90° C. Additional 0.5 eq. of morpholine wad added to push reaction to completion. The solvent was removed in vacuo. The resulting brown residue was proved to be the pure methyl [(4Z)-4-[1-(benzylamino)-2-morpholin-4-ylethylidene]-1-(2-chlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate (0.37 g). Yield 98%. MS (ESI+): 483.9; MS (ESI−): 481.8.

Workup

  1. additionThe mixture of the
  2. customreaction to completion
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f3ed1fa44bbf4354b130a69622f754bd
Source dataset
uspto-grants-2015_04
Patent number
US09012449B2

Reaction notes

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