Azepane → HCID 11500844, compound

HRID 1820144Notes

Reaction equation

HRID 1820144 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC(C)([O-])C.[Na+].[NH:35]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.Br[C:43]1[CH:48]=[C:47]([CH3:49])[C:46]([NH:50][C:51](=[O:58])[CH2:52][CH:53]2[CH2:57][CH2:56][CH2:55][CH2:54]2)=[C:45]([CH3:59])[CH:44]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[N:35]1([C:43]2[CH:48]=[C:47]([CH3:49])[C:46]([NH:50][C:51](=[O:58])[CH2:52][CH:53]3[CH2:57][CH2:56][CH2:55][CH2:54]3)=[C:45]([CH3:59])[CH:44]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 8119AzepaneHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 11507840N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamideHCID 23676156Sodium t-butoxide

Product 1

HCID 11500844HCID 11500844, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Bis(dibenzylideneacetone)palladium (2.8 mg) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (3.8 mg) were mixed in dry toluene (2.5 mL) under argon for 5 minutes. To this mixture were added sodium tert-butoxide (6 mg), azacycloheptane (7.5 mg) and N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide (1p, 15 mg) and the reaction was heated to 110° C. in a sealed 4 mL vial under argon for 48 hours. The reaction mixture was concentrated in vacuo, sodium hydroxide (2 M, 1.5 mL) was added and the product was extracted with isopropyl acetate (3×1.5 mL). The combined organic phases were dried over magnesium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 7.9 mg (50% yield) of the title compound as an oil. LC-MS-TOF (m/z) 329 (MH+); tR=2.08, (UV, ELSD) 90%, 99%.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, sodium hydroxide (2 M, 1.5 mL)
  2. additionwas added
  3. extractionthe product was extracted with isopropyl acetate (3×1.5 mL)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-15509d4dd43e4553b70dd64df7aee6d7
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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