Dimethylamine → HCID 59003120, compound

HRID 2353887Notes

Reaction equation

HRID 2353887 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([C:30](=[O:32])[CH3:31])[CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[C:9]2[CH:33]=[C:34](Br)[C:35]([Cl:37])=[CH:36][C:8]1=2)=[O:6])([CH3:3])[CH3:2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+].[CH3:79][NH:80][CH3:81]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:30]([N:14]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=1)[CH:10]1[CH2:11][CH2:12][CH2:13][N:7]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])[C:8]2[CH:36]=[C:35]([Cl:37])[C:34]([N:80]([CH3:81])[CH3:79])=[CH:33][C:9]1=2)(=[O:32])[CH3:31]

Participants

8

Reactant 4

HCID 674Dimethylamine2×HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 59003215Isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-7-bromo-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

Product 1

HCID 59003120HCID 59003120, compoundYield 52.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-7-bromo-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.075 g, 0.119 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.003 g, 0.0029 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.006 g, 0.012 mmol), sodium tert-butoxide (0.029 g, 0.298 mmol) and dimethylamine (0.071 mL, 0.143 mmol, 2.0 M in THF) in toluene (0.5 mL) in a 10 mL microwave vessel and irradiate at 110° C. for 20 min (50 W). Add a large excess of dimethylamine (2 mL, 4 mmol, 2.0 M in THF) and irradiate at 110° C. for 20 min. Dilute the cooled mixture with ethyl acetate (25 mL) and filter through Celite. Remove the filtrate solvent under reduced pressure and purify the residue using chromatography on silica gel, eluting with hexanes/ethyl acetate (60:40), to provide the title compound as an off-white solid (0.037 g, 52%): ESI MS 594 (M+H).

Workup

  1. customirradiate at 110° C. for 20 min
  2. filtrationfilter through Celite
  3. customRemove the filtrate solvent under reduced pressure
  4. custompurify the residue
  5. washeluting with hexanes/ethyl acetate (60:40)

Sources & evidence

ORD record
ord-7d0a19ffe7e5440cb2fef9edd2051794
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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