Diisopropyl Ether → HCID 131734743、化合物

HRID 1775453ノート

反応式

HRID 1775453 の反応式
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]

参加物

10

反応物 6

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

生成物 1

HCID 131734743HCID 131734743、化合物

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb8a015441d94704a2407982867d52e9
出典データセット
uspto-grants-2016_02
特許番号
US09260445B2

反応ノート

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