Formic Acid → HCID 67147726, 화합물

HRID 506805노트

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HRID 506805 반응식
[CH3:1][O:2][C:3]1N=[C:7]2[C:9]([C:13]3[N:24]([S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])[C:16]4[N:17]=[CH:18][CH:19]=[C:20]([CH:21]=[N:22]O)[C:15]=4[CH:14]=3)=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[O:35][CH3:36].[CH:37](O)=O>C(O)C.O.[Zn]>[O:2]([C:3]1[CH:37]=[C:7]2[C:6](=[CH:5][C:4]=1[O:35][CH3:36])[N:11]([CH3:12])[CH:10]=[C:9]2[C:13]1[N:24]([S:25]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)(=[O:26])=[O:27])[C:16]2=[N:17][CH:18]=[CH:19][C:20]([CH2:21][NH2:22])=[C:15]2[CH:14]=1)[CH3:1]

참가 물질

6

반응물 2

HCID 284Formic AcidHCID 1363864872-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde oxime

생성물 1

HCID 67147726HCID 67147726, 화합물

시약·촉매·용매 3

HCID 23994Zinc촉매2회HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of 0.56 g of [2-(5,6-dimethoxy-1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-carbaldehyde oxime in 30 cm3 of ethanol and 25 cm3 of water, at a temperature in the region of 20° C., is added 0.216 g of zinc and 12 cm3 of concentrated formic acid. A further 0.216 g of zinc is added and the mixture is stirred for a further 24 hours. The reaction medium is stirred at this same temperature for 24 hours. The reaction medium is filtered through Celite and the filtrate is concentrated under reduced pressure. The residue obtained is purified by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05, then dichloromethane/methanol/triethylamine 100/10/1, then dichloromethane/methanol/28% aqueous ammonia 100/10/2 by volume as eluents, Ar). The residue obtained is again purified by flash-pack chromatography (SiO2, dichloromethane/methanol/28% aqueous ammonia 460/40/1.5 by volume as eluents, Ar). 0.03 g of [2-(5,6-dimethoxy1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]methylamine is obtained with the following characteristics:

후처리

  1. stirringThe reaction medium is stirred at this same temperature for 24 hours
  2. filtrationThe reaction medium is filtered through Celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by flash-pack chromatography (SiO2, dichloromethane/methanol 95/05
  6. customThe residue obtained
  7. customis again purified by flash-pack chromatography (SiO2, dichloromethane/methanol/28% aqueous ammonia 460/40/1.5 by volume as eluents, Ar)

출처 및 근거

ORD 기록
ord-4148336754c242ebac22504df2382a54
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786114B2

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