2-(Phenylhydrazono)-propanedioyl dichloride → N-Isopropyl-2-[5-(4-methoxy-benzyl)-2,4-dioxo-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-(4-methoxy-phenyl)-acetamide

HRID 1599087Notes

Reaction equation

HRID 1599087 reaction equation
[CH:1]([N:4]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:5](=[O:24])[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([CH3:3])[CH3:2].[C:33]1([NH:39][N:40]=[C:41]([C:45](Cl)=[O:46])[C:42](Cl)=[O:43])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[CH:1]([N:4]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:5](=[O:24])[CH2:6][N:7]1[C:42](=[O:43])[C:41](=[N:40][NH:39][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:45](=[O:46])[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]1=2)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 105144812-(Phenylhydrazono)-propanedioyl dichlorideHCID 18929570N-isopropyl-2-[2-(4-methoxybenzylamino)-phenylamino]-N-(4-methoxy phenyl)-acetamide

Product 1

HCID 86752412N-Isopropyl-2-[5-(4-methoxy-benzyl)-2,4-dioxo-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-(4-methoxy-phenyl)-acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-isopropyl-2-[2-(4-methoxybenzylamino)-phenylamino]-N-(4-methoxy phenyl)-acetamide (3.25 g, 7.51 mmol) in THF (50 mL) cooled in an ice bath (<5° C.) was added 2-(phenyl-hydrazono) propandioyl dichloride (1.84 g, 7.51 mmol) in THF (50 mL) dropwise over 20 minutes. After complete addition, the solution was allowed to warm to room temperature and stirred overnight. The solvent was evaporated under reduced pressure and the resultant oil was dissolved in ethyl acetate (300 mL), washed with saturated sodium bicarbonate solution (100 mL) and brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (4.55 g, 7.51 mmol) as a yellow oil: 1H NMR (300 MHz, CDCl3): d 11.46 (s, 0.5H), 10.69 (s, 0.5H), 7.56-6.95 (m, 15H), 6.77-6.66 (m, 2H), 5.34 (m, 1H), 5.05 (m, 1H), 4.79 (m, 1H), 4.34-4.08 (m, 2H), 3.86 (s, 2H), 3.74 (s, 3H), 3.72 (s, 3H), 1.11 (m, 6H); TLC (EtOAc/Hexanes(2:3)): Rf =0.30.

Workup

  1. additionAfter complete addition
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe resultant oil was dissolved in ethyl acetate (300 mL)
  4. washwashed with saturated sodium bicarbonate solution (100 mL) and brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e693ef1b91534185a56325e0ac0f55c6
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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