1-Hydroxybenzotriazole → N-(3-(pyrimidin-5-yl)-phenyl)-2,3-dimethyl-1H-indole-7-carboxamide

HRID 1835462노트

반응식

HRID 1835462 반응식
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=2[C:12]([OH:14])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[N:37]1[CH:42]=[C:41]([C:43]2[CH:44]=[C:45]([CH:47]=[CH:48][CH:49]=2)[NH2:46])[CH:40]=[N:39][CH:38]=1>ClCCl>[N:37]1[CH:42]=[C:41]([C:43]2[CH:44]=[C:45]([NH:46][C:12]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[NH:3][C:2]([CH3:1])=[C:10]4[CH3:11])=[O:14])[CH:47]=[CH:48][CH:49]=2)[CH:40]=[N:39][CH:38]=1

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37026102,3-Dimethyl-7-indolecarboxylic acidHCID 71620493-Pyrimidin-5-ylaniline

생성물 1

HCID 23503684N-(3-(pyrimidin-5-yl)-phenyl)-2,3-dimethyl-1H-indole-7-carboxamide수율 68.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 2,3-dimethylindole-7-carboxylic acid (95 mg) and 1-hydroxybenzotriazole (81 mg) in dichloromethane (3 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg), and the mixture was stirred for 5 minutes. After adding 3-(pyrimidin-5-yl)aniline (94 mg) and 4-dimethylinopyridine (92 mg), the mixture was stirred for 24 hours. The mixture was diluted with dichloromethane and washed with water and brine. The organic layer 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-(pyrimidin-5-yl)-phenyl)-2,3-dimethyl-1H-indole-7-carboxamide (117 mg, 68.4%).

후처리

  1. stirringthe mixture was stirred for 24 hours
  2. washwashed with water and brine
  3. dry with materialThe organic layer 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-3c26dbca05024175b655374961393faf
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06770667B1

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