Diisopropylethylamine → 2,5-dichloro-N-[2-[2-(2,5-difluorophenyl)ethoxy]ethanimidoyl]pyridine-3-carboxamide

HRID 2100479노트

반응식

HRID 2100479 반응식
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[F:44][C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][C:46]=1[CH2:52][CH2:53][O:54][CH2:55][C:56]([NH2:58])=[NH:57]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:58][C:56](=[NH:57])[CH2:55][O:54][CH2:53][CH2:52][C:46]1[CH:47]=[C:48]([F:51])[CH:49]=[CH:50][C:45]=1[F:44])=[O:6]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27360852,5-Dichloropyridine-3-carboxylic acidHCID 670990362-[2-(2,5-Difluoro-phenyl)-ethoxy]-acetamidine hydrochloride

생성물 1

HCID 1405200772,5-dichloro-N-[2-[2-(2,5-difluorophenyl)ethoxy]ethanimidoyl]pyridine-3-carboxamide수율 96.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2,5-Dichloronicotinic acid (50 mg, 260 μmol), TBTU (88 mg, 273 μmol) and DIPEA (130 μl, 781 μmol) were added to a solution of 2-[2-(2,5-difluoro-phenyl)-ethoxy]-acetamidine hydrochloride (65 mg, 260 μmol) in DMF (1 ml). The solution was stirred for 72 h at ambient temperature and poured onto ice water/dichloromethane 1/1. The layers were separated, the aqueous layer was extracted two times with dichloromethane, the combined extracts were washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure yielded 2,5-dichloro-N-{2-[2-(2,5-difluoro-phenyl)-ethoxy]-1-imino-ethyl}-nicotinamide (97 mg, 250 μmol; 96%) as orange oil which was used in the next step without further purification. MS: m/e=388.2 [M+H+].

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted two times with dichloromethane
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-4b8494a269964381bb0fee044b9f2c29
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572801B2

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