Morpholine → HCID 21254991, compound

HRID 636445Notes

Reaction equation

HRID 636445 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]1([S:13]([C:16]2[C:17]([CH2:33][CH3:34])=[N:18][N:19]3[C:24]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)=[CH:23][C:22](Cl)=[N:21][C:20]=23)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[C:7]1([S:13]([C:16]2[C:17]([CH2:33][CH3:34])=[N:18][N:19]3[C:24]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)=[CH:23][C:22]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[N:21][C:20]=23)(=[O:14])=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 21255002HCID 21255002, compound

Product 1

HCID 21254991HCID 21254991, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.26 ml (3 mmol) of morpholine in 5 ml of DMF was added to a solution of 0.50 g (1.2 mmol) of 3-benzenesulphonyl-5-chloro-2-ethyl-7-(4-methyl-piperazin-1-yl)-pyrazolo[1,5-a]pyrimidine in 15 ml of DMF and stirred at 100° for hr. After cooling to RT the reaction solution was evaporated and the residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2, and the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (SiO2, CH2Cl2/MeOH 15:1) and crystallization from EtOH yielded 0.45 g (80%) of 3-benzenesulphonyl-2-ethyl-7-(4-methyl-piperazin-1-yl)-5-morpholin-4-yl-pyrazolo[1,5-a]-pyrimidine as colorless crystals, m.p.>250°.

Workup

  1. customwas evaporated
  2. customthe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with CH2Cl2
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (SiO2, CH2Cl2/MeOH 15:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-244ad3cda33b495a8c0397ba6be27ac6
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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