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Diisopropylamine → 2-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide

HRID 278035
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HRID 278035 반응식
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[CH:6]([NH2:15])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:16]1[CH:21]=[CH:20][C:19]([C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([C:31](O)=[O:32])=[CH:30][C:24]=3[N:23]=2)=[CH:18][CH:17]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(NC(C)C)(C)C>CN(C)C=O>[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[CH:6]([NH:15][C:31]([C:29]1[CH:28]=[CH:27][C:25]2[NH:26][C:22]([C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)=[N:23][C:24]=2[CH:30]=1)=[O:32])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 7912DiisopropylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 697111551-[1,3,4]Oxadiazole-2-yl-3-phenylpropylamineHCID 178524160HCID 178524160, 화합물

생성물 1

HCID 1785232812-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

220 mg of 1-[1,3,4]oxadiazole-2-yl-3-phenylpropylamine were dissolved in 10 ml of dry dimethylformamide at RT, treated with 260 mg of 2-pyridin-4-yl-1H-benzimidazol-5-carboxylic acid, 350 mg of TOTU, and 0.15 ml of diisopropylamine, and stirred at RT for 4 h. The reaction mixture was concentrated, the residue was taken up in ethyl acetate, and the mixture was washed successively with water, saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel using dichloromethane/methanol (8/1) and yielded 2-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide, which melts at 103° C. with decomposition.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. washthe mixture was washed successively with water, saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-3026923cd43a4aef8ee7c8a1e3428a01
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06358978B1

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