Ethylenediamine → Lazabemide

HRID 1769272

반응식

HRID 1769272 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH2:9]([NH2:12])[CH2:10][NH2:11].[CH3:13][O-:14].[Na+]>C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[ClH:1].[NH2:11][CH2:10][CH2:9][NH:12][C:13]([C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1)=[O:14]

참가 물질

6

반응물 3

HCID 3301EthylenediamineHCID 276852,5-DichloropyridineHCID 10942334Sodium Methoxide

생성물 2

HCID 313Hydrochloric AcidHCID 71307Lazabemide수율 75%

시약·촉매·용매 1

HCID 812191,3-Bis(diphenylphosphino)propane촉매

실험 절차

The amidation of 5 g (33.8 mmol) of 2,5-dichloropyridine in the presence of 12.1 g (202 mmol) of ethylenediamine, 8.8 mg of palladium-dichloro-bis(acetonitrile) and 21 mg of 1,3-bis(diphenylphosphino)propane is carried out at 110° in a manner analogous to Example 1. After the addition of 1.91 g (35.5 mmol) of sodium methylate and evaporation of the reaction mixture there are obtained, by extraction with 3N hydrochloric acid and subsequent basification of the acidic-aqueous solution, 5.05 g (75%) of N-(2-aminoethyl)-5-chloropyridine-2-carboxamide; content according to HPLC: 98.2 wt.%, content of N,N'-ethylene-bis(5-chloro-2-pyridinecarboxamide): <1% (GC). Conversion of the free base with hydrogen chloride in methanol into the hydrochloride and crystallization from methanol/ether yields N-(2-aminoethyl)-5-chloropyridine-2-carboxamide hydrochloride as white crystals, m.p. 191°-195°.

후처리

  1. customis carried out at 110° in a manner analogous to Example 1

출처 및 근거

ORD 기록
ord-761cdcc3a657437d808d8f6f01e84fbf
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380861

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