N,N'-Dimethylethylenediamine → HCID 67281262, compound

HRID 1516327Notes

Reaction equation

HRID 1516327 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15](I)[CH:16]=3)[CH2:11][C@@H:10]2[OH:19])=[O:7])=[CH:4][CH:3]=1.[C:22]([N:29]1[CH2:34][CH2:33][NH:32][C:31](=[O:35])[CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].CNCCNC>CN1CCCC1=O.C(OCC)(=O)C.[Cu]I>[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N:32]4[CH2:33][CH2:34][N:29]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:30][C:31]4=[O:35])[CH:16]=3)[CH2:11][C@@H:10]2[OH:19])=[O:7])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 67280582HCID 67280582, compound

Product 1

HCID 67281262HCID 67281262, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

Purge a mixture of 4-fluoro-N-[(1S,2S)-2-hydroxy-6-iodo-indan-1-yl]benzamide (8.70 g, 21.9 mmol), 4-N-boc-2-oxo-piperazine (4.61 g, 22.3 mmol), and potassium carbonate (6.12 g, 43.8) in N-methylpyrrolidone (100 mL) with nitrogen gas. Add copper (I) iodide (2.11 g, 11.0 mmol) and sym-dimethylethylene diamine (2.34 mL, 21.9 mmol). Seal the flask with a septum and stir at 100° C. for 6 hr. Cool the mixture to room temperature and dilute with ethyl acetate (100 mL). Wash the organic portion with water (3×100 mL), then brine, and then dry over sodium sulfate, filter, and concentrate to dryness. Purify the residue by column chromatography (120 g silica, 2 to 5% methanol/chloroform) to obtain the title compound (7.63 g, 74%). LC-ES/MS m/z 470 [M+H]+.

Workup

  1. customPurge
  2. customSeal the flask with a septum
  3. temperatureCool the mixture to room temperature
  4. washWash the organic portion with water (3×100 mL)
  5. dry with materialbrine, and then dry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate to dryness
  8. customPurify the residue by column chromatography (120 g silica, 2 to 5% methanol/chloroform)

Sources & evidence

ORD record
ord-ab5ae1e8a9ad44f793965ffab3375521
Source dataset
uspto-grants-2012_07
Patent number
US08227468B2

Reaction notes

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