Triethylamine → HCID 57993726, compound

HRID 1695067Notes

Reaction equation

HRID 1695067 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=[CH:14]\[C:15]1[NH:19][C:18]([CH3:20])=[C:17]([C:21]([OH:23])=O)[C:16]=1[CH3:24])([O-:3])=[O:2].Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[NH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[NH:61][C:62](=[O:73])[C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH2:70][CH2:71][NH2:72])=[N:65][CH:64]=1>[Cl-].[Na+].O.CN(C=O)C>[NH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[NH:61][C:62](=[O:73])[C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH2:70][CH2:71][NH:72][C:21]([C:17]2[C:16]([CH3:24])=[C:15](/[CH:14]=[C:7]3\[C:8](=[O:13])[NH:9][C:10]4[C:6]\3=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=4)[NH:19][C:18]=2[CH3:20])=[O:23])=[N:65][CH:64]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57993739N-(2-aminophenyl)-6-(2-aminoethylamino)nicotinamideHCID 67279867HCID 67279867, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 57993726HCID 57993726, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-(5-Nitro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (327 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 (383 mg, 66%) as a yellow solid. LC-MS (m/z) 581 (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-80955bc88e4842c694e1f99d7098efd8
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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