1-Hydroxybenzotriazole → N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-[2,2']bithiophenyl-5-carboxamide

HRID 1835470

反応式

HRID 1835470 の反応式
[S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=[C:2]1[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:36][N:37]1[C:41]([C:42]2[CH:43]=[C:44]([CH:46]=[CH:47][CH:48]=2)[NH2:45])=[CH:40][N:39]=[C:38]1[CH3:49]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:49][C:38]1[N:37]([CH3:36])[C:41]([C:42]2[CH:43]=[C:44]([NH:45][C:6]([C:5]3[S:1][C:2]([C:9]4[S:10][CH:11]=[CH:12][CH:13]=4)=[CH:3][CH:4]=3)=[O:8])[CH:46]=[CH:47][CH:48]=2)=[CH:40][N:39]=1

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 1509652,2'-Bithiophene-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235036623-(1,2-dimethyl-1H-imidazol-5-yl)aniline

生成物 1

HCID 69899339N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-[2,2']bithiophenyl-5-carboxamide収率 61.7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of [2,2′]bithiophenyl-5-carboxylic acid (105 mg) and 1-hydroxybenzotriazole (81 mg) in dichloromethane (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg) and the mixture was stirred for 15 minutes. After adding 3-(1,2-dimethylimidazol-5-yl)aniline (94 mg) and 4-dimethylaminopyridine (92 mg), the mixture was stirred for 24 hours. The mixture was diluted with dichloromethane and washed with water and brine. The mixture was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 3% methanol in dichloromethane to give N-[3-(2,3-dimethyl-3H-imidazol-4-yl)-phenyl]-[2,2′]bithiophenyl-5-carboxamide (117 mg, 61.6%).

後処理

  1. stirringthe mixture was stirred for 24 hours
  2. washwashed with water and brine
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluting with 3% methanol in dichloromethane

出典と根拠

ORDレコード
ord-368687d2cde84cb3af405a9b0a251b07
出典データセット
uspto-grants-2004_08
特許番号
US06770667B1

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