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

HRID 21592

반응식

HRID 21592 반응식
[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]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric Acid2회HCID 24532Lithium amideHCID 13837937ethyl 3-(diethylamino)-5-methoxy-1H-indole-2-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-37fa8988fca1478b905c4ec599fe19b5
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424329

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