3,3-Dimethylbutylamine → 5-Cyano-6-(4-ethoxy-2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid (3,3-dimethyl-butyl)-amide

HRID 252470Notes

Reaction equation

HRID 252470 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)[C:20]([O:30][CH2:31][CH3:32])=[CH:19][C:18]=1[N+:33]([O-:35])=[O:34])[CH:4]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH2:5][CH2:6][C:7](O)=[O:8])#[N:2].[CH3:36][C:37]([CH3:42])([CH3:41])[CH2:38][CH2:39][NH2:40].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.O>[CH3:36][C:37]([CH3:42])([CH3:41])[CH2:38][CH2:39][NH:40][C:7](=[O:8])[CH2:6][CH2:5][CH:4]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:3]([C:1]#[N:2])=[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)[C:20]([O:30][CH2:31][CH3:32])=[CH:19][C:18]=1[N+:33]([O-:35])=[O:34]

Participants

7

Reactant 4

HCID 197093,3-DimethylbutylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672684215-Cyano-6-(4-ethoxy-2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid

Product 1

HCID 672691075-Cyano-6-(4-ethoxy-2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid (3,3-dimethyl-butyl)-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-cyano-6-(4-ethoxy-2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid (160 mg, 0.33 mmol), 3,3-dimethylbutylamine (40 mg, 0.4 mmol), HBTU (155 mg, 0.4 mmol) and DIEA (150 μL) in DMF (10 mL) was stirred at room temperature overnight. Water was then added, and the resulting mixture was extracted with methylene chloride (3×). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The resulting crude mixture was purified by chromatography (silica gel, 20-50% ethyl acetate in heptane) to yield a yellow oil.

Workup

  1. extractionthe resulting mixture was extracted with methylene chloride (3×)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude mixture was purified by chromatography (silica gel, 20-50% ethyl acetate in heptane)
  7. customto yield a yellow oil

Sources & evidence

ORD record
ord-8817859bed1642ebae9d66631b9b99ae
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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