Triethylamine → n-(2-Aminophenyl)-6-(2-(2-(((5-nitro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamide

HRID 1695068Notes

Reaction equation

HRID 1695068 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[N:14][N:15]=[CH:16]C1(C)CC(C)(C(O)=O)CN1)([O-:3])=[O:2].Cl.[CH2:28](N=C=NCCCN(C)C)[CH3:29].O[C:40]1C2N=NNC=2C=CC=1.C([N:51]([CH2:54][CH3:55])[CH2:52][CH3:53])C.[NH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[NH:63][C:64](=[O:75])[C:65]1[CH:70]=[CH:69][C:68]([NH:71][CH2:72][CH2:73][NH2:74])=[N:67][CH:66]=1.[Cl-].[Na+].[OH2:78]>CN(C=O)C>[NH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[NH:63][C:64](=[O:75])[C:65]1[CH:70]=[CH:69][C:68]([NH:71][CH2:72][CH2:73][NH:74][C:28]([C:29]2[C:55]([CH3:40])=[C:54]([CH:16]=[N:15][N:14]=[C:7]3[C:6]4[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[NH:9][C:8]3=[O:13])[NH:51][C:52]=2[CH3:53])=[O:78])=[N:67][CH:66]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57417360Sodium chloride; waterHCID 57993739N-(2-aminophenyl)-6-(2-aminoethylamino)nicotinamideHCID 137252516HCID 137252516, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 136610855n-(2-Aminophenyl)-6-(2-(2-(((5-nitro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamideYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(((5-Nitro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acid (355 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and N-(2-aminophenyl)-6-(2-aminoethylamino)nicotinamide (284 mg, 1.05 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (450 mg, 74%) as a red solid. LC-MS (m/z) 609 (M+1).

Workup

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-332d5946d7484ace947eb4241d28c671
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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