1-Methylpiperazine → HCID 69430551, compound

HRID 1593430Notes

Reaction equation

HRID 1593430 reaction equation
CS([C:5]1[N:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:13]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[C:27](=[O:31])[CH2:26][CH2:25]4)[CH:12]=2)=[CH:7][N:6]=1)(=O)=O.[CH3:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>CN(C)C=O>[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([C:5]2[N:10]=[CH:9][C:8]([C:11]3[O:15][C:14]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)=[C:13]([C:22]4[CH:23]=[C:24]5[C:28](=[CH:29][CH:30]=4)[C:27](=[O:31])[CH2:26][CH2:25]5)[CH:12]=3)=[CH:7][N:6]=2)[CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 69430943HCID 69430943, compound

Product 1

HCID 69430551HCID 69430551, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of the product from Step 6 (0.15 g, 0.35 mmol) in dry dimethylformamide (2 ml) was treated with N-methylpiperazine (0.077 ml, 0.70 mmol) and heated at 90° C. for 2 hours. After cooling to room temperature the reaction mixture was applied to a SCX column and washed with methanol then a mixture of 0.880 ammonia/methanol (1:9). The basic fractions were combined and chromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane solution (0.5:4.5:95) to afford the title compound (0.09 g, 57%); MS(ES+) m/e 452 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. washwashed with methanol
  3. additiona mixture of 0.880 ammonia/methanol (1:9)
  4. customchromatographed on silica gel eluting with 0.880 ammonia/methanol/dichloromethane solution (0.5:4.5:95)

Sources & evidence

ORD record
ord-71720ae5ea994d6c8443fd54217af460
Source dataset
uspto-grants-2007_11
Patent number
US07297694B2

Reaction notes

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