Water → HCID 68407704, compound

HRID 888024Notes

Reaction equation

HRID 888024 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:17]([O:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH2:31])=[O:23])([CH3:20])([CH3:19])[CH3:18].O>CN(C=O)C>[C:17]([O:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:16][CH:15]=1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 7365324-(4-Methylpiperazin-1-yl)benzoic acid

Product 1

HCID 68407704HCID 68407704, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1-Methylpiperazin-4-yl)benzoic acid (250 mg, 1.13 mmol) and 1-(N-t-butoxycarbonylamino)-2-aminobenzene (Method 17, 331 mg, 1.59 mmol) were dissolved in DMF (3 ml). 4-(4,6-dimethoxy-1,3,5-triazinyl-2-yl)-4-methylmorpholinium chloride (Method 18, 313 mg, 1.13 mmol) was added and the resulting solution was stirred for 20 hours at ambient temperature. The solution was poured into water and extracted several times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (eluting with 99:1→9:1 dichloromethane:methanol) to afford the title compound as a colourless gum which crystallised on trituration (240 mg, 52%); Mass Spectrum: M+H+ 411.

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography (eluting with 99:1→9:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-7c0bd5cc1f1740a98d12a5ef92bb78b9
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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