Morpholine → HCID 178499639, compound

HRID 1253444Notes

Reaction equation

HRID 1253444 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1=[N:6][N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:8](=[O:21])/[C:9]/1=[C:10](\[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[CH2:11]Cl.[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>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1=[N:6][N:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:8](=[O:21])/[C:9]/1=[C:10](\[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[CH2:11][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]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-a532461ca0cc45acaeff6cb4fabc077c
Source dataset
uspto-grants-2013_06
Patent number
US08455485B2

Reaction notes

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