Dimethylamine → HCID 68850320, compound

HRID 1984049Notes

Reaction equation

HRID 1984049 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C@H:13]3[CH2:17][C@:10]2([CH3:18])[CH2:11][CH2:12]3)=[O:7])=[CH:4][C:3]=1[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].[CH3:30][NH:31][CH3:32].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[K+]>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].CN(C)C=O>[CH3:30][N:31]([CH3:32])[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C@H:13]3[CH2:17][C@:10]2([CH3:18])[CH2:11][CH2:12]3)=[O:7])=[CH:4][C:3]=1[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 634876Binap, (A+-)-HCID 23665647Potassium tert-butoxideHCID 68852883HCID 68852883, compound

Product 1

HCID 68850320HCID 68850320, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-3-(morpholinosulfonyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)benzamide (2.4.AaBa, 0.400 g, 0.824 mmol), dimethylamine (Cd, 2 mL 2M in THF), and 3 mL N,N-dimethylformamide were mixed. Tris(dibenzylideneacetone)dipalladium(0) (0.08 g, 0.08 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.05 g, 0.08 mmol), and potassium tert-butoxide (0.9 g, 8 mmol) were then added. The reaction was heated to at 100° C. for 24 hours. After aqueous workup and acidic extraction, the organic layer was evaporated to yield a yellow solid. The product was then purified by SiO2 chromatography (5-20% ethyl acetate/hexane) to yield 4-(dimethylamino)-3-(morpholinosulfonyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)benzamide (2E) as an off-white solid (180 mg, 49% yield). MS analysis (m+1)=450.6.

Workup

  1. extractionAfter aqueous workup and acidic extraction
  2. customthe organic layer was evaporated
  3. customto yield a yellow solid
  4. customThe product was then purified by SiO2 chromatography (5-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-60757d7100384af69548a40c0cf8be44
Source dataset
uspto-grants-2009_06
Patent number
US07544676B2

Reaction notes

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