Ethyl Acetate → (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide

HRID 2201087

반응식

HRID 2201087 반응식
Cl.[NH2:2][C@H:3]([CH2:7][CH3:8])[C:4]([NH2:6])=[O:5].[Cl:9][C:10]1[C:15]([C:16]#[N:17])=[CH:14][C:13]([F:18])=[C:12](Cl)[N:11]=1.CCN(C(C)C)C(C)C.CCOC(C)=O>CN1C(=O)CCC1>[Cl:9][C:10]1[N:11]=[C:12]([NH:2][C@H:3]([CH2:7][CH3:8])[C:4]([NH2:6])=[O:5])[C:13]([F:18])=[CH:14][C:15]=1[C:16]#[N:17]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 16218339(2R)-2-aminobutanamide hydrochloride

생성물 1

HCID 86666160(R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide수율 98.2%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To the mixture of (R)-(−)-2-aminobutanamide hydrochloride (1.00 g, 7.2 mmol) and 2,6-dichloro-5-fluoro-3-pyridinecarbonitrile (0.92 g, 4.8 mmol) in 40 mL NMP added DIEA (2.5 mL, 14.4 mmol). The mixture was then sent to 100° C. for stirring for 1 h. The mixture was cooled to RT, and to it was poured 300 mL EtOAc. The mixture was washed with brine four times. The organic phase was dried, concentrated and purified using silica flash column (70% EtOAc-30% DCM) to isolate (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide (1.21 g, 98% yield).

후처리

  1. customwas then sent to 100° C.
  2. washThe mixture was washed with brine four times
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. custompurified

출처 및 근거

ORD 기록
ord-b54ef00c6f0e484a94626fc0ab96e84e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359375B2

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