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

HRID 900828ノート

反応式

HRID 900828 の反応式
[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.[Br:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]([C:64]2[NH:68][N:67]=[C:66]([NH2:69])[N:65]=2)([CH3:63])[CH3:62])=[CH:57][CH:56]=1>C(#N)C>[Br:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]([C:64]2[N:65]=[C:66]([NH2:69])[N:67]([C:21]([C:2]3([CH3:1])[CH2:17][C:10]4([N+:18]([O-:20])=[O:19])[C:9]5[C:4]([CH:3]3[C:16]3[C:11]4=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:5][CH:6]=[CH:7][CH:8]=5)=[O:23])[N:68]=2)([CH3:63])[CH3:62])=[CH:57][CH:56]=1

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 586702735-[1-(4-bromophenyl)-1-methylethyl]-1H-1,2,4-triazol-3-amineHCID 596985749-Nitro-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid

生成物 1

HCID 586703343-[1-(4-bromophenyl)-1-methylethyl]-1-[(15-methyl-8-nitrotetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaen-15-yl)carbonyl]-1H-1,2,4-triazol-5-amine収率 93%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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 (31 mg, 0.10 mmol, prepared according to WO04009017), 1-hydroxybenzotriazole (20 mg, 0.15 mmol), and N-ethyl-N,N-diisopropylamine (0.15 mL) in anhydrous acetonitrile (1.5 mL) was added EDCI (39 mg, 0.2 mmol) at RT under argon. After the mixture was stirred at RT for 5 min, 5-[1-(4-bromophenyl)-1-methylethyl]-1H-1,2,4-triazol-3-amine (28 mg, 0.1 mmol) was added. The reaction mixture was stirred at RT for 2 h 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 53 mg (93% yield) of the title compound as a white solid which was used as such for the subsequent step without further purification.

後処理

  1. stirringThe reaction mixture was stirred at RT for 2 h 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

出典と根拠

ORDレコード
ord-62082d91f66a4cbe84672052c5a41229
出典データセット
uspto-grants-2008_04
特許番号
US07361654B2

反応ノート

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