3,3-Dimethylbutanoyl chloride → HCID 25005966, compound

HRID 1443899Notes

Reaction equation

HRID 1443899 reaction equation
[CH:1]1[C:10]2[C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][C:2]=1[NH2:18].[C:19]([CH2:23][C:24](Cl)=[O:25])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[CH:1]1[C:10]2[C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][C:2]=1[NH:18][C:24](=[O:25])[CH2:23][C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 44248849HCID 44248849, compound

Product 1

HCID 25005966HCID 25005966, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-amine (0.27 g, 1.1 mmol), t-butylacetyl chloride (0.18 mL, 1.3 mmol) and poly-(4-vinylpyridine) (700 mg) in dichloromethane (18 mL) was stirred at room temperature overnight. The resin was removed by filtration and washed with dichloromethane. The filtrate was concentrated and the product was purified by flash column chromatography (elution with 30% ethyl acetate-hexane) to provide 0.20 g of N-5,6,9,10,11,12-hexahydro-4H,8H-cyclohepta[4,5]pyrrolo[3,2,1-ij]quinolin-2-yl-3,3-dimethylbutanamide as a white solid. MS (ESI) m/z 339.

Workup

  1. customThe resin was removed by filtration
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated
  4. customthe product was purified by flash column chromatography (elution with 30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-f0c779eff2ab41558ec52f09cd45c988
Source dataset
uspto-grants-2010_02
Patent number
US07662831B2

Reaction notes

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