Ammonium Chloride → 4-(2,3-diaminophenyl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

HRID 1533755Notes

Reaction equation

HRID 1533755 reaction equation
[NH2:1][C:2]1[C:44]([N+:45]([O-])=O)=[CH:43][CH:42]=[CH:41][C:3]=1[C:4]([NH:6][C:7]1[CH:38]=[CH:37][C:10]([C:11]([N:13]([CH3:36])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:28])=[O:12])=[CH:9][C:8]=1[O:39][CH3:40])=[O:5].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:2]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][C:3]=1[C:4]([NH:6][C:7]1[CH:38]=[CH:37][C:10]([C:11]([N:13]([CH3:36])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:28])=[O:12])=[CH:9][C:8]=1[O:39][CH3:40])=[O:5]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 183552134-(2-amino-3-nitrobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

Product 1

HCID 183547944-(2,3-diaminophenyl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideYield 362.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(2-amino-3-nitrobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (3.88 g) in ethanol (40 ml) were added a solution of ammonium chloride (385 mg) in water (10 ml) and iron powder (2.01 g) and the mixture was stirred at 100° C. for 2 hours. The mixture was filtered through a bed of celite and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate and the solution was washed with aqueous saturated sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate and the solution was concentrated in vacuo to give 4-(2,3-diaminobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide as a yellow powder 13.42 g).

Workup

  1. filtrationThe mixture was filtered through a bed of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washthe solution was washed with aqueous saturated sodium bicarbonate solution and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-1e2297bee53243b6862f0b1e1c99ec5b
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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