N-Methylcyclohexylamine → 5-Cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid cyclohexyl-methyl-amide

HRID 502865Notes

Reaction equation

HRID 502865 reaction equation
[C:1]([C:3](=[CH:16][C:17]1[CH:22]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:20]=[CH:19][C:18]=1[N+:30]([O-:32])=[O:31])[CH:4]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH2:5][CH2:6][C:7]([OH:9])=O)#[N:2].[CH3:33][NH:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:35]1([N:34]([CH3:33])[C:7](=[O:9])[CH2:6][CH2:5][CH:4]([CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[C:3]([C:1]#[N:2])=[CH:16][C:17]2[CH:22]=[C:21]([O:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:20]=[CH:19][C:18]=2[N+:30]([O-:32])=[O:31])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 7514N-MethylcyclohexylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672694525-Cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid

Product 1

HCID 672693405-Cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid cyclohexyl-methyl-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid (0.87 g, 2 mmol), N-methylcyclohexylamine (0.26 mL, 2 mmol), HBTU (1.13 g, 3 mmol), DIPEA (1.2 mL, 7 mmol) in DMF (20 mL) was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture. The solution washed with saturated aqueous NaHCO3 solution. The organic phase was separated and dried with MgSO4, and filtered. The solvent was removed in vacuo to yield the title compound as an oil.

Workup

  1. washThe solution washed with saturated aqueous NaHCO3 solution
  2. customThe organic phase was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4c3d833126d444168f6bce87a78dc29d
Source dataset
uspto-grants-2010_08
Patent number
US07776882B2

Reaction notes

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