Piperazine → HCID 66745112, compound

HRID 1959403Notes

Reaction equation

HRID 1959403 reaction equation
[C:1]([O:5][C:6]([N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:9]1[C:10]([C:16]2[N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>CN(C=O)C.CCOC(C)=O.O>[C:1]([O:5][C:6]([N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:9]1[C:10]([C:16]2[N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:11][C:12]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 86662083HCID 86662083, compound

Product 1

HCID 66745112HCID 66745112, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 2-[3-[bis(tert-butoxycarbonyl)amino]-6-bromo-pyrazin-2-yl]indole-1-carboxylate (100 mg, 0.1696 mmol) and piperazine (146.1 mg, 1.696 mmol) in DMF (2 mL) was heated at 100° C. for 30 minutes and then allowed to cool to ambient temperature. The reaction was diluted with EtOAc/water and the organic layer washed further with water (2×), dried (MgSO4) and concentrated in vacuo. The material was used crude in the next step (quantitative yield assumed). MS (ES+) 595.09

Workup

  1. temperatureto cool to ambient temperature
  2. washthe organic layer washed further with water (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efa7c3f3fd4d41aa873c15811ef8596e
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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