Diethyl cyanophosphonate → HCID 86759184, compound

HRID 1169360Notes

Reaction equation

HRID 1169360 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][CH:14]([C:18](O)=[O:19])[CH2:13][C:12]=3[CH:21]=2)=[CH:4][CH:3]=1.[CH3:22][N:23]([CH2:30][C:31]1[CH:37]=[CH:36][C:34](N)=[CH:33][CH:32]=1)[CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(P(=O)(OCC)OCC)#[N:39].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[CH3:22][N:23]([CH2:30][C:31]1[CH:37]=[CH:36][CH:34]=[CH:33][C:32]=1[C:14]1([C:18]([NH2:39])=[O:19])[CH2:13][C:12]2[CH:21]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)[CH:9]=[CH:10][C:11]=2[O:17][CH2:16][CH2:15]1)[CH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 22989988HCID 22989988, compound

Product 1

HCID 86759184HCID 86759184, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Into a solution of 7-(4-methylphenyl)-2,3,4,5-tetrahydro-1-benzooxepine-4-carboxylic acid (141 mg) and 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline (110 mg) in DMF (4 ml) were added under ice cooling diethyl cyanophosphonate (0.08 ml) and triethylamine (0.08 ml). After being stirred at 0° C. for 30 minutes and at room temperature for 8 hours, an aqueous solution of sodium bicarbonate was added into the reaction mixture under ice cooling. The resulting mixture was extracted with ethyl acetate, and the extract was washed with an aqueous saturated solution of sodium chloride. The extract was dried with anhydrous magnesium sulfate and was then concentrated under reduced pressure. The residue was subjected to purification using silica gel column chromatography (ethyl acetate/hexane=4/1) and further to recrystallization from ethyl acetate/hexane to obtain N-[4-[(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)phenyl]-7-(4-methylphenyl)-2,3,4,5-tetrahydro-1-benzooxepine-4-carboxamide (compound 25) (43 mg) as colorless crystals.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washthe extract was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialThe extract was dried with anhydrous magnesium sulfate
  4. concentrationwas then concentrated under reduced pressure
  5. customThe residue was subjected to purification
  6. customfurther to recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-966001b26e0045c4b345ce5baf715383
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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