Cyclopropylamine → HCID 71268295, compound

HRID 1519688Notes

Reaction equation

HRID 1519688 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:33])[N:22]([CH:24]([C:29]([NH:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26])[CH3:23])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C>[CH:1]1([NH:4][CH2:5][C:7]2[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][C:18]([C:21](=[O:33])[N:22]([CH:24]([C:29]([NH:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26])[CH3:23])=[CH:17][CH:16]=3)=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86679262HCID 86679262, compound

Product 1

HCID 71268295HCID 71268295, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

Cyclopropylamine (0.15 g) and acetic acid (0.16 g) were added to a chloroform (20 mL) solution of 1-formyl-4-[(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)ethynyl]benzene (1.0 g) as obtained in Example 10-(5), and the mixture was stirred for 2.5 hours at room temperature. Then, sodium triacetoxyborohydride (0.89 g) was added, and the mixture was stirred for 15 hours at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and then the mixture was extracted with chloroform. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=34/66→1/100) to obtain 1-[(cyclopropylamino)methyl]-4-[(4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}phenyl)ethynyl]benzene (colorless foam) (0.84 g, 74%).

Workup

  1. customas obtained in Example 10-(5)
  2. stirringthe mixture was stirred for 15 hours at room temperature
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThen, the desiccant was filtered out
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=34/66→1/100)

Sources & evidence

ORD record
ord-a71fef421d7248aeac5ce94d8bdf0a50
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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