Water → HCID 11373433, compound

HRID 2354172Notes

Reaction equation

HRID 2354172 reaction equation
[CH:1](N(CC)C(C)C)(C)C.[CH:10]1([NH:13][C:14]([C:16]2[CH:17]=[CH:18][C:19]([CH3:35])=[C:20]([NH:22][C:23](=[O:34])[C:24]3[CH:29]=[CH:28][C:27](F)=[CH:26][C:25]=3[N+:31]([O-])=O)[CH:21]=2)=[O:15])[CH2:12][CH2:11]1.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.O>CS(C)=O>[CH:10]1([NH:13][C:14](=[O:15])[C:16]2[CH:17]=[CH:18][C:19]([CH3:35])=[C:20]([N:22]3[C:23](=[O:34])[C:24]4[C:25](=[CH:26][C:27]([N:40]5[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]5)=[CH:28][CH:29]=4)[N:31]=[CH:1]3)[CH:21]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 66918928HCID 66918928, compound

Product 1

HCID 11373433HCID 11373433, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Diisopropylethylamine (0.30 ml) was added to a stirred mixture of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-4-fluoro-2-nitrobenzamide (0.30 g) and N-methylpiperazine (0.28 ml) in DMSO (0.5 ml). The mixture was heated to 90° C. and stirred for 16 hours. The reaction mixture was poured into water (100 ml), the resulting solid was filtered, washed with water, diethyl ether and redissolved in methylene chloride. The organic phase was dried (diatomaceous earth column) and evaporated to give the title compound as a solid (0.23 g); NMR Spectrum: (DMSOd6) 0.58 (m, 2H), 0.69 (m, 2H), 2.24 (s, 3H), 2.29 (s, 3H), 2.46 (m, 4H), 2.85 (m, 1H), 3.36 (m, 4H), 7.30 (m, 2H), 7.45 (d, 1H), 7.61 (m, 1H), 7.67 (d, 1H), 7.83 (s, 1H), 8.39 (d, 1H), 10.03 (s, 1H); Mass Spectrum: M+H+ 438.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with water, diethyl ether
  3. dissolutionredissolved in methylene chloride
  4. customThe organic phase was dried (diatomaceous earth column)
  5. customevaporated

Sources & evidence

ORD record
ord-56e34c8be1ad43f2b67dbd17815ba2a9
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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