Diisopropylethylamine → 3-(1-Cyanocyclopropanecarboxamido)biphenyl-2-carboxamide

HRID 2036831노트

반응식

HRID 2036831 반응식
[C:1]([C:3]1([C:6]([OH:8])=O)[CH2:5][CH2:4]1)#[N:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:44]=1[C:55]([NH2:57])=[O:56]>C(Cl)Cl>[C:1]([C:3]1([C:6]([NH:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:44]=2[C:55]([NH2:57])=[O:56])=[O:8])[CH2:5][CH2:4]1)#[N:2]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27332591-Cyanocyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66965572HCID 66965572, 화합물

생성물 1

HCID 670558893-(1-Cyanocyclopropanecarboxamido)biphenyl-2-carboxamide수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-cyanocyclopropanecarboxylic acid (0.75 g, 7 mmol) in DCM (40 mL) was added HATU (3.5 g, 10 mmol) and DIPEA (3.4 mL, 20 mmol). After stirring at room temperature for 1 h, 3-aminobiphenyl-2-carboxamide (from example 218: 1 g, 5 mmol) was added and the reaction mixture stirred for an additional 16 h. The reaction mixture was washed with water and the organic phase dried, filtered, concentrated under reduced pressure and purified by silica gel chromatography (60% ethyl acetate in hexanes) to provide 3-(1-cyanocyclopropanecarboxamido)biphenyl-2-carboxamide (0.75 g, 74% yield) as a white solid. LCMS Method T: retention time 1.53 min; [M+1]=306.2.

후처리

  1. stirringthe reaction mixture stirred for an additional 16 h
  2. washThe reaction mixture was washed with water
  3. customthe organic phase dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel chromatography (60% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-8627cf1220c5435daa228f61f03c2100
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575184B2

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