Diisopropyl Ether → HCID 131734743, 화합물

HRID 1775453노트

반응식

HRID 1775453 반응식
C(NCC[C:7]1[C:15]2[C:10](=[CH:11][C:12]([F:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C:8]=1[C:19]([OH:21])=O)(=O)C.[Cl-].[NH4+].O[N:25]1[C:29]2[CH:30]=CC=CC=2N=N1.Cl.C([N:37]=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+].[CH:51]([O:54]C(C)C)(C)[CH3:52]>C(OCC)(=O)C.C(N(CC)CC)C.C(#N)C>[C:51]([NH:25][CH2:29][CH2:30][N:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][CH3:17])=[C:12]([F:18])[CH:11]=2)[CH:7]=[C:8]1[C:19]([NH2:37])=[O:21])(=[O:54])[CH3:52]

참가 물질

10

반응물 6

HCID 7914Diisopropyl EtherHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89933016HCID 89933016, 화합물

생성물 1

HCID 131734743HCID 131734743, 화합물

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 3-(2-acetamidoethyl)-6-fluoro-5-methoxy-1H-indole-2-carboxylic acid (200 mg), ammonium chloride (110 mg), 1-hydroxybenzotriazole (140 mg), and acetonitrile (4.00 mL) were added triethylamine (0.300 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (200 mg), followed by stirring at room temperature overnight. To the mixture was added an aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform, and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4 to 9:1). To the obtained crude product was added ethyl acetate, followed by heating. Then, diisopropylether was added thereto, followed by stirring at room temperature. The resulting solid was collected by filtration and dried under reduced pressure to obtain 3-(2-acetamidoethyl-6-fluoro-5-methoxy-1H-indole-2-carboxamide (153 mg) as a white solid.

후처리

  1. extractionfollowed by extraction with chloroform
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4 to 9:1)
  4. customTo the obtained crude product
  5. temperatureby heating
  6. stirringby stirring at room temperature
  7. filtrationThe resulting solid was collected by filtration
  8. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-bb8a015441d94704a2407982867d52e9
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260445B2

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