Triethylamine → 7-(2-furyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide

HRID 565944Notes

Reaction equation

HRID 565944 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]2[O:15][CH2:14][CH2:13][C:12]([C:16]([OH:18])=O)=[CH:11][C:10]=2[CH:19]=1.[CH3:20][N:21]([CH2:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]2[O:15][CH2:14][CH2:13][C:12]([C:16]([NH:33][C:32]3[CH:34]=[CH:35][C:29]([CH2:28][N:21]([CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH3:20])=[CH:30][CH:31]=3)=[O:18])=[CH:11][C:10]=2[CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 184725847-(2-Furyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid

Product 1

HCID 217157087-(2-furyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamideYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2-furyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid (0.15g), 4-(N-methyl-N-(tetrahydropyran-4-yl)aminomethyl)aniline (0.15g) and triethylamine (0.25ml) in dimethylformamide (10ml) was added diethyl cyanophosphate (0.13ml) under ice-cooling, and the mixture was stirred under nitrogen atmosphere at room temperature over night. The solvent was evaporated, and the residue was purified with silica gel column (methanol/ethyl acetate/triethylamine) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 7-(2-furyl)-N-(4-((N-tetrahydropyran-4-yl-N-methylamino)methyl)-phenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 148) (0.1g) as brown crystals.

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated
  3. customthe residue was purified with silica gel column (methanol/ethyl acetate/triethylamine)
  4. customto give crude crystals, which
  5. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-badb0a27fa2a4a5abfa6920e5a5fc83d
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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