Morpholine → HCID 70109056, compound

HRID 1379035Notes

Reaction equation

HRID 1379035 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:10]2=[C:11]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:13][N:9]2[CH2:8][CH2:7][NH:6]1)=[O:4].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(N(CC)CC)C>ClCCCl>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[C:11]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:10]3[N:5]([C:3](=[O:4])[CH2:2][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[NH:6][CH2:7][CH2:8][N:9]3[N:13]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 70107211HCID 70107211, compound

Product 1

HCID 70109056HCID 70109056, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-chloroacetyl-7-(4-fluorophenyl)-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (80 mg, 0.215 mmol), morpholine (37 mg, 0.430 mmol), and triethylamine (22 mg, 0.215 mmol) in 1,2-dichloroethane (2 ml) was stirred for 24 hours at ambient temperature. After dilution of dichloromethane, the mixture was washed with an aqueous saturated sodium bicarbonate solution, and brine. The organic phase was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluent:ethyl acetate ethyl acetate/methanol; 20/1), and the obtained oil was crystallized from diisopropyl ether to give 7-(4-fluorophenyl)-2-morpholinoacetyl-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (50 mg).

Workup

  1. washAfter dilution of dichloromethane, the mixture was washed with an aqueous saturated sodium bicarbonate solution, and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (eluent:ethyl acetate ethyl acetate/methanol; 20/1)
  5. customthe obtained oil was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b028d61defad43e69db83d09f7d5cffe
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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