Diisopropylethylamine → HCID 58001077, compound

HRID 658046Notes

Reaction equation

HRID 658046 reaction equation
F[P-](F)(F)(F)(F)F.CN([C:11](N(C)C)=[N+:12]1[C:16]2C=CC(Cl)=C[C:15]=2[N+:14]([O-])=N1)C.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[O:61])[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][N:42]([CH2:55][CH2:56][CH2:57][N:58]([CH3:60])[CH3:59])[C:43]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]([OH:54])=O)=[CH:48][CH:47]=2)=[O:44])=[CH:37][CH:36]=1.[CH3:62]NN(NC)CCN.C(N(CC)C(C)C)(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[O:61])[C:35]1[CH:36]=[CH:37][C:38]([CH2:41][N:42]([CH2:55][CH2:56][CH2:57][N:58]([CH3:60])[CH3:59])[C:43]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]([NH:14][CH2:15][CH2:16][N:12]([CH3:11])[CH3:62])=[O:54])=[CH:48][CH:47]=2)=[O:44])=[CH:39][CH:40]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 57160625HCID 57160625, compoundHCID 58001142HCID 58001142, compoundHCID 178484290HCID 178484290, compound

Product 1

HCID 58001077HCID 58001077, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[Bis(dimethylamino)methylene]-5-chloro-1H-benzo triazolium 3-oxide hexafluorophosphate (49 mg, 0.067 mmol) was added to a suspension of N-(2-aminophenyl)-4-[3-(4-carboxyphenyl)-1-(3-dimethylaminopropyl)ureidomethyl]benzamide (Compound No. 4-1, 33 mg, 0.067 mmol), N,N-dimethylaminoethylenediamine (0.30 mL, 2.8 mmol) and N,N-diisopropylethylamine (0.023 mL, 0.13 mmol) in DMF (5.0 mL), and then the mixture was stirred at room temperature for 80 minutes. Saturated aqueous sodium hydrogen carbonate solution (30 mL) was added thereto, the whole was extracted with ethyl acetate (20 mL) twice, and then the organic layer was washed with brine (30 mL) twice. The organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 21 mg of the title compound as colorless oil. (Yield 57%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (20 mL) twice
  2. washthe organic layer was washed with brine (30 mL) twice
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-df14fdf0258f438eb4de7653a2bf40e2
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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