1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[(15-methyl-8-nitrotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-yl)carbonyl]-3-(1-naphthyl)-1H-1,2,4-triazol-5-amine

HRID 906823Notes

Reaction equation

HRID 906823 reaction equation
[CH3:1][C:2]1([C:21]([OH:23])=O)[CH2:17][C:10]2([N+:18]([O-:20])=[O:19])[C:11]3[C:16]([CH:3]1[C:4]1[C:9]2=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.CCN=C=NCCCN(C)C.[C:54]1([C:64]2[NH:68][N:67]=[C:66]([NH2:69])[N:65]=2)[C:63]2[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH:57]=[CH:56][CH:55]=1>C(#N)C>[CH3:1][C:2]1([C:21]([N:67]2[C:66]([NH2:69])=[N:65][C:64]([C:54]3[C:63]4[C:58](=[CH:59][CH:60]=[CH:61][CH:62]=4)[CH:57]=[CH:56][CH:55]=3)=[N:68]2)=[O:23])[CH2:17][C:10]2([N+:18]([O-:20])=[O:19])[C:11]3[C:16]([CH:3]1[C:4]1[C:9]2=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 36979375-(naphthalen-1-yl)-4H-1,2,4-triazol-3-amineHCID 596985749-Nitro-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid

Product 1

HCID 591273591-[(15-methyl-8-nitrotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-yl)carbonyl]-3-(1-naphthyl)-1H-1,2,4-triazol-5-amineYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 15-methyl-8-nitrotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylic acid (22 mg, 0.07 mmol, prepared according to WO04009017), 1-hydroxybenzotriazole (14 mg, 0.11 mmol), and N-ethyl-N,N-diisopropylamine (0.25 mL) in anhydrous acetonitrile (2 mL) was added EDCI (34 mg, 0.18 mmol) at RT under argon. After the mixture was stirred at RT for 10 min, 5-(naphthalen-1-yl)-1H-1,2,4-triazol-3-amine (22 mg, 0.1 mmol) was added. The reaction mixture was stirred at RT overnight and at 80° C. for 1 h. After the solvents were removed, the residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution. The aqueous solution was extracted with methylene chloride. The combined organic solutions were dried (Na2SO4), concentrated and purified by silica gel chromatography to give 33 mg (94% yield) of the title compound as a white solid. (M+H)+=502.26.

Workup

  1. stirringThe reaction mixture was stirred at RT overnight and at 80° C. for 1 h
  2. customAfter the solvents were removed
  3. customthe residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
  4. extractionThe aqueous solution was extracted with methylene chloride
  5. dry with materialThe combined organic solutions were dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c089844e80bd49d9bde02155ce4204c5
Source dataset
uspto-grants-2011_09
Patent number
US08013004B2

Reaction notes

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