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

HRID 1835470

반응식

HRID 1835470 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-368687d2cde84cb3af405a9b0a251b07
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06770667B1

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