Acetic Acid → 3-(Diethylamino)-5-methoxy-1H-indole-2-carboxamide, monohydrochloride

HRID 21592

反応式

HRID 21592 の反応式
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5]=1[C:15](OCC)=[O:16])[CH3:2].[NH2-:22].[Li+].C(O)(=O)C.[ClH:28]>CCOCC>[ClH:28].[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5]=1[C:15]([NH2:22])=[O:16])[CH3:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric Acid2 回HCID 24532Lithium amideHCID 13837937ethyl 3-(diethylamino)-5-methoxy-1H-indole-2-carboxylate

生成物 1

HCID 1317190223-(Diethylamino)-5-methoxy-1H-indole-2-carboxamide, monohydrochloride収率 36%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Prepared from ethyl 3-(diethylamino)-5-methoxy-1H-indole-2-carboxylate (Unangst PC, et al., J. Heterocyclic Chem. 1987;24:817) and lithium amide by the procedure described in Example 18, with the exception that dilute acetic acid is substituted for 1.0N HCl during the wash of the ethyl acetate extracts. The crude product is purified by flash chromatography (silica gel, 30% ethyl acetate in dichloromethane elution) to give a foam. The foam is dissolved in ether and treated with gaseous HCl to provide the product salt in 36% yield after recrystallization from acetonitrile; mp 244° C.-dec.

後処理

  1. washwash of the ethyl acetate
  2. customThe crude product is purified by flash chromatography (silica gel, 30% ethyl acetate in dichloromethane elution)
  3. customto give a foam
  4. customto provide the product salt in 36% yield
  5. customafter recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-37fa8988fca1478b905c4ec599fe19b5
出典データセット
uspto-grants-1995_06
特許番号
US05424329

関連ノート

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