Diisopropylethylamine → HCID 59784370, compound

HRID 470346Notes

Reaction equation

HRID 470346 reaction equation
[Na+].[NH2:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O-:7])=O.[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[CH2:18][CH2:17]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:2][C:3]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][N:19]2[CH2:18][CH2:17][N:16]([CH3:15])[CH2:21][CH2:20]2)=[CH:25][CH:26]=1)=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 242554804-[2-(4-Methylpiperazin-1-yl)ethyl]anilineHCID 59785142Sodium 2-amino-3-nitrobenzoate

Product 1

HCID 59784370HCID 59784370, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-amino-3-nitro-benzoic acid sodium salt (205 mg, 1.0 mmol), 4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenylamine (219 mg, 1.0 mmol) and HATU (400 mg, 1.05 mmol) in DMF (2 mL) was added DIEA (0.52 mL, 388 mg, 3.0 mmol). The reaction mixture was stirred at room temperature for 1 h and heated at 70° C. for 1 h, and then evaporated under reduced pressure. The residue was purified by chromatography (50:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (300 mg, 78%). 1H NMR (MeOH-d4) δ 2.44 (s, 3H), 2.50-2.85 (12H), 6.74 (dd, J=9 Hz and 9 Hz, 1H), 7.23 (d, J=9 Hz, 2H), 7.58 (d, J=9 Hz, 2H), 7.91 (d, J=9 Hz, 1H), 8.29 (d, J=9 Hz, 1H). ESI-MS m/z 384.5 (MH+).

Workup

  1. temperatureheated at 70° C. for 1 h
  2. customevaporated under reduced pressure
  3. customThe residue was purified by chromatography (50:10:1 CH2Cl2/MeOH/28% aqueous NH4OH)

Sources & evidence

ORD record
ord-2c59aadaa8ae48b1b955b40c53d4d96a
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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