Triethylamine → Cyclopropanecarboxylic acid {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amide

HRID 1950340Notes

Reaction equation

HRID 1950340 reaction equation
COC1C=CC(C2C[CH2:27][C:26]3C(=CC=[C:24]([O:29]C)[CH:25]=3)C2)=C(NCCC2C=CC(O)=CC=2)C=1.[Si:31]([O:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][NH:47][C:48]2[CH:53]=[C:52]([O:54][CH3:55])[CH:51]=[CH:50][C:49]=2[CH:56]2[CH2:65][CH2:64][C:63]3[C:58](=[CH:59][CH:60]=[C:61]([O:66][CH3:67])[CH:62]=3)[CH2:57]2)=[CH:41][CH:40]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].C(N(CC)CC)C.C1(C(Cl)=O)CC1>O1CCCC1>[Si:31]([O:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:45][CH2:46][N:47]([C:48]2[CH:53]=[C:52]([O:54][CH3:55])[CH:51]=[CH:50][C:49]=2[CH:56]2[CH2:65][CH2:64][C:63]3[C:58](=[CH:59][CH:60]=[C:61]([O:66][CH3:67])[CH:62]=3)[CH2:57]2)[C:24]([CH:25]2[CH2:26][CH2:27]2)=[O:29])=[CH:43][CH:44]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 579340414-{2-[5-Methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamino]ethyl}phenolHCID 66625834{2-[4-(Tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

Product 1

HCID 57933985Cyclopropanecarboxylic acid {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized from 4-{2-[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamino]ethyl}phenol according to an analogous synthetic method to Example 201, to a solution of the resulting {2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (2.3 g) in tetrahydrofuran (50 ml) was added triethylamine (895 mg), cyclopropanecarbonyl chloride (693 mg) was added dropwise thereto on an ice bath followed by stirring for 30 minutes at room temperature. The solution was extracted with ethyl acetate, then sequentially washed with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (2.3 g).

Workup

  1. additionwas added dropwise
  2. customon an ice bath followed
  3. extractionThe solution was extracted with ethyl acetate
  4. washsequentially washed with a saturated aqueous solution of sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-617df61bdebe4139b94fb680ab26906d
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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