Water → HCID 22291924, compound

HRID 968115Notes

Reaction equation

HRID 968115 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][N:33]=1)[C:5]([NH:7][C:8]1[CH:30]=[CH:29][C:11]2[CH2:12][CH2:13][C:14]3[C:15]([C:26]([NH2:28])=[O:27])=[N:16][N:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:18]=3[C:10]=2[CH:9]=1)=[O:6].[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.O>CN(C)C(=O)C>[F:25][C:22]1[CH:23]=[CH:24][C:19]([N:17]2[C:18]3[C:10]4[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]5[CH:31]=[CH:32][N:33]=[C:2]([N:38]6[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]6)[CH:3]=5)[CH:30]=[CH:29][C:11]=4[CH2:12][CH2:13][C:14]=3[C:15]([C:26]([NH2:28])=[O:27])=[N:16]2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 22291543HCID 22291543, compound

Product 1

HCID 22291924HCID 22291924, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

The material from step 1 (2.17 mmoles) and N-methyl piperazine (32.9 mmoles) were dissolved in 5.0 mL N,N-dimethylacetamide. The reaction mixture was then placed under nitrogen and stirred in an oil bath at 100° C. for 88 h. The mixture was partially stripped of solvent then added to water, filtered, and washed with water. The solid was then dissolved in acetonitrile, decolorized with decolorizing carbon, and dried over anhydrous MgSO4. The solvent was stripped, then the solid residue was recrystallized from acetonitrile. Mp: 277-279° C. 1H NMR (400 MHz, d6-DMSO): δ 2.17 (s, 3H); 2.35 (t, 4H, J=5 Hz); 2.82-2.95 (m, 4H); 3.47 (t, 4H, J=5 Hz); 6.85 (d, 1H, J=5 Hz); 7.01 (s, 1H); 7.21-7.44 (m, 6H); 7.50-7.59 (m, 3H); 8.16 (d, 1H, J=5 Hz); 10.10 (s, 1H). 13C NMR (DMSO-d6, 100 MHz): δ 20.32, 29.69, 45.20, 46.46, 55.00, 105.43, 111.23, 115.50, 117.07, 117.30, 120.66, 121.37, 126.54, 128.60, 128.69, 129.48, 133.36, 136.82, 136.85, 137.70, 139.71, 143.19, 144.36, 148.89, 159.88, 161.37, 163.81, 164.44, 165.15. M+1=526.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. dissolutionThe solid was then dissolved in acetonitrile
  4. dry with materialdried over anhydrous MgSO4
  5. customthe solid residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b63391d4d86b4c42ab1123b17db74bfa
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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