Diethyl Ether → HCID 178521739, compound

HRID 1797151Notes

Reaction equation

HRID 1797151 reaction equation
CN1CCOCC1.[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[CH:18]1([C:21]2[CH:25]=[C:24]([NH2:26])[NH:23][N:22]=2)[CH2:20][CH2:19]1.C(OCC)C>ClC>[CH:18]1([C:21]2[CH:25]=[C:24]([NH:26][C:13](=[O:14])[C:12]3[CH:16]=[CH:17][C:9]([Br:8])=[CH:10][CH:11]=3)[NH:23][N:22]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 79724-MethylmorpholineHCID 685154-Bromobenzoyl chlorideHCID 178507266HCID 178507266, compound

Product 1

HCID 178521739HCID 178521739, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6327Methyl ChlorideSolvent

Procedure

122 mg (loading 1.91 mmol/g, 0.233 mmol) of polystyrene supported N-methylmorpholine were suspended in 4 ml of chloromethane and then treated with 25.6 mg (0.117 mmol) of 4-bromobenzoyl chloride followed by 4.8 mg (0.039 mmol) of 3-cyclopropyl-5-amino-pyrazole. After 48 hours under stirring at room temperature the resin was separated by filtration and washed with 2 ml of dichloromethane. The filtrate was evaporated to dryness, the residue re-dissolved in 4 ml of dichloromethane and 100 mg of polystyrene supported trisamine were added. After 48 hours or stirring at room temperature the resin was filtered, washed with 2 ml of dichloromethane and concentrated to give, after triturating with diethylether, 9.3 mg (78% yield) of the title compound.

Workup

  1. customwas separated by filtration
  2. washwashed with 2 ml of dichloromethane
  3. customThe filtrate was evaporated to dryness
  4. dissolutionthe residue re-dissolved in 4 ml of dichloromethane
  5. additionwere added
  6. waitAfter 48 hours
  7. stirringstirring at room temperature the resin
  8. filtrationwas filtered
  9. washwashed with 2 ml of dichloromethane
  10. concentrationconcentrated
  11. customto give

Sources & evidence

ORD record
ord-8d58305e75a74c79be5f8ed5fd6d45f7
Source dataset
uspto-grants-2006_04
Patent number
US07034049B1

Reaction notes

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