Water → HCID 66919038, compound

HRID 641949Notes

Reaction equation

HRID 641949 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:22]([O-:24])=[O:23])=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:13]([O:15][CH3:16])=[O:14])=[O:8].[CH:25]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([CH3:27])[CH3:26].C(N(CC)C(C)C)(C)C.O>CS(C)=O>[CH3:20][C:19]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[NH:9][C:7](=[O:8])[C:6]1[CH:21]=[C:2]([N:31]2[CH2:32][CH2:33][N:28]([CH:25]([CH3:27])[CH3:26])[CH2:29][CH2:30]2)[CH:3]=[CH:4][C:5]=1[N+:22]([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 780131-IsopropylpiperazineHCID 81531DiisopropylethylamineHCID 52693948HCID 52693948, compound

Product 1

HCID 66919038HCID 66919038, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of methyl 3-[(5-fluoro-2-nitrobenzoyl)amino]-4-methylbenzoate (8 g) in DMSO (24 ml) was added N-isopropylpiperazine (3.4 g) and N,N-diisopropylethylamine (4.7 ml) and the reaction stirred at room temperature for 6 hours. Water (200 ml) was added and the resultant solid collected by filtration, washed with water (×3) and dried in vacuo at 50° C. for 16 hours to yield methyl 4-methyl-3-{[5-(4-isopropylpiperazin-1-yl)-2-nitrobenzoyl]amino}benzoate as a yellow solid (10.7 g); NMR Spectrum: (DMSOd6) 0.99 (d, 6H), 2.34 (s, 3H), 2.55 (m, 4H), 2.71 (m, 1H), 3.50 (m, 4H), 3.85 (s, 3H), 7.07 (m, 2H), 7.39 (d, 1H), 7.71 (m, 1H), 8.06 (d, 1H), 8.20 (m, 1H), 9.96 (s, 1H); Mass Spectrum: M+H+ 441.

Workup

  1. filtrationthe resultant solid collected by filtration
  2. washwashed with water (×3)
  3. customdried in vacuo at 50° C. for 16 hours

Sources & evidence

ORD record
ord-251ceb7c61124478a38cc2be471fb171
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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