2,3-Diaminonaphthalene → HCID 21105298, compound

HRID 1354273Notes

Reaction equation

HRID 1354273 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.[NH2:14][C:15]1[C:24]([NH2:25])=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C>CN(C)C=O.O.C(OCC)(=O)C.C(N(CC)CC)C>[NH2:14][C:15]1[C:24]([NH:25][C:11]([C:6]2[NH:7][C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[O:13])=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1

Participants

9

Reactant 4

HCID 698722,3-DiaminonaphthaleneHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 21105298HCID 21105298, compoundYield 24.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-chloroindole-2-carboxylic acid (247 mg), 2,3-diaminonaphthalene (200 mg), 1-hydroxybenzotriazole hydrate (221 mg), 1-[3-dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (315 mg) and triethylamine (447 mg) in N,N-dimethylformamide was stirred under nitrogen at room temperature for 3 h. The reaction mixture was diluted with water before extraction with ethyl acetate (three times). The combined organic extracts were washed sequentially with saturated aqueous ammonium chloride solution, water and saturated aqueous sodium bicarbonate solution (three times each), dried over anhydrous magnesium sulfate and evaporated under vacuum to yield a solid. The solid was triturated with chloroform and then dried under vacuum to obtain the title compound as a tan solid (102 mg).

Workup

  1. washThe combined organic extracts were washed sequentially with saturated aqueous ammonium chloride solution, water and saturated aqueous sodium bicarbonate solution (three times each),
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under vacuum
  4. customto yield a solid
  5. customThe solid was triturated with chloroform
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c265c2e78d234c8a8b11a79d5de2e542
Source dataset
uspto-grants-2007_05
Patent number
US07223786B2

Reaction notes

Loading…