1-Methylpiperazine → HCID 22291961, compound

HRID 457307Notes

Reaction equation

HRID 457307 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:18]4[C:17]5[CH:19]=[C:20]([NH:23][C:24](=[O:33])[C:25]6[C:30]([Cl:31])=[CH:29][N:28]=[C:27](Cl)[CH:26]=6)[CH:21]=[CH:22][C:16]=5[CH2:15][CH2:14][C:13]=4[C:12]([C:34]([NH2:36])=[O:35])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:18]4[C:17]5[CH:19]=[C:20]([NH:23][C:24](=[O:33])[C:25]6[C:30]([Cl:31])=[CH:29][N:28]=[C:27]([N:41]7[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]7)[CH:26]=6)[CH:21]=[CH:22][C:16]=5[CH2:15][CH2:14][C:13]=4[C:12]([C:34]([NH2:36])=[O:35])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 22291587HCID 22291587, compound

Product 1

HCID 22291961HCID 22291961, compoundYield 46%

Conditions

Temperature
100 °C

Procedure

A mixture of the title compound of Example 211 (1.2 g, 0.0023 mol) and N-methylpiperazine (4.6 mL, 0.046 mol) was heated at 100° C. in a sealed tube for 24 h. The completion of the reaction was checked by HPLC. After removal of the volatiles under vacuum, the residue was partitioned between water and CH2Cl2. The organic layer was washed an additional time with water and dried over MgSO4. The crude product mixture was purified by chromatography on silica gel using CH2Cl2/MeOH: 12/1 to 10/2 to give 0.62 g of the title product, yield: 46%. Mp: 305–307° C. 1H NMR (400 MHz, d6-DMSO): δ 2.18 (s, 3H), 2.34–2.35 (d, 2H, J=5 Hz), 2.89–2.91 (m, 4H), 3.49 (d, 2H, J=5 Hz), 6.08 (s, 2H), 6.91–7.03 (m, 3H), 7.1 (d, 1H, J=2 Hz), 7.24–7.3 (m, 3H), 7.38–7.41 (dd, 1H, J=8.3 Hz, 2 Hz), 7.49 (s, 1H), 8.13 (s, 1H), 10.33 (s, 1H). M+1=587.

Workup

  1. customAfter removal of the volatiles under vacuum
  2. customthe residue was partitioned between water and CH2Cl2
  3. washThe organic layer was washed an additional time with water
  4. dry with materialdried over MgSO4
  5. customThe crude product mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bcd2b70bd8a648eca8933e1cc5c23086
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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