HCID 86602860, compound → HCID 86602863, compound

HRID 1517705Notes

Reaction equation

HRID 1517705 reaction equation
[C:1]([Cu])#[N:2].[CH2:4]([NH:6][C:7](=[O:9])[O-:8])[CH3:5].[CH3:10][O:11][C:12]1[C:13](Br)=[CH:14][C:15]2[CH:16]([CH3:24])[CH:17]3[CH2:21][NH:20][CH2:19][CH:18]3[C:22]=2[CH:23]=1>CN(C=O)C.O>[CH2:4]([NH:6][C:7](=[O:8])[O-:9])[CH3:5].[CH3:10][O:11][C:12]1[C:13]([C:1]#[N:2])=[CH:14][C:15]2[CH:16]([CH3:24])[CH:17]3[CH2:21][NH:20][CH2:19][CH:18]3[C:22]=2[CH:23]=1

Participants

5

Reactant 2

HCID 86602860HCID 86602860, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86602863HCID 86602863, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

CuCN (68 mg, 0.85 mmol) was added to a solution of N-ethylcarbamate-5-methoxy-6-bromo-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 30, Step A) (60 mg, 0.17 mmol) in DMF (1.7 mL), and stirred overnight at 100° C. The reaction mixture was diluted with EtOAC and H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via a silica plug eluting with Hexanes/EtOAc (2/1, v/v). MS calculated for C17H20N2O3+H: 301, observed: 301.

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified via a silica plug
  5. washeluting with Hexanes/EtOAc (2/1

Sources & evidence

ORD record
ord-bb9db3acf79a43fca49341052c6a0b7b
Source dataset
uspto-grants-2012_07
Patent number
US08232311B2

Reaction notes

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