Diisopropylethylamine → N-(4-Aminothiophen-3-yl)-4-[1-(2-dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzamide

HRID 217642Notes

Reaction equation

HRID 217642 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][CH:5]([NH:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH2:23][CH2:22]2)=[O:17])[C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=1.Cl.Cl.[NH2:31][C:32]1[C:36]([NH2:37])=[CH:35][S:34][CH:33]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[NH2:37][C:36]1[C:32]([NH:31][C:10](=[O:11])[C:9]2[CH:8]=[CH:7][C:6]([CH:5]([NH:15][C:16]([NH:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[CH2:24][CH2:23][CH2:22]4)=[O:17])[CH2:4][CH2:3][N:2]([CH3:28])[CH3:1])=[CH:14][CH:13]=2)=[CH:33][S:34][CH:35]=1

Participants

7

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 127073423,4-Diaminothiophene dihydrochlorideHCID 670498974-[1-(2-Dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzoic acid

Product 1

HCID 67049894N-(4-Aminothiophen-3-yl)-4-[1-(2-dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzamideYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[1-(2-dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzoic acid (Reference Compound No. 11-1, 77 mg, 0.20 mmol), 3,4-diaminothiophene dihydrochloride (45 mg, 0.24 mmol), N,N-diisopropylethylamine (77 μL, 0.44 mmol) and HATU (90 mg, 0.24 mmol) in DMF (2.0 mL) was stirred at room temperature overnight. Water (30 mL) was added to the reaction solution, and then the whole was extracted with ethyl acetate (30 mL) three times. The organic layer was washed with water (30 mL) and brine (30 mL), dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel (NH-modified silica gel) column chromatography (chloroform-methanol) to give 55 mg of the title compound as a brown amorphous product. (Yield 58%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (30 mL) three times
  2. washThe organic layer was washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel (NH-modified silica gel) column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-d281162df8b2459b9141a742f2525742
Source dataset
uspto-grants-2012_06
Patent number
US08198271B2

Reaction notes

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