Water → 1-(6-Chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclopentanecarboxamide

HRID 2201152

반응식

HRID 2201152 반응식
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[C:4](Cl)[N:3]=1.Cl.[NH2:13][C:14]1([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:13][C:14]2([C:19]([NH2:21])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:5]([F:10])=[CH:6][C:7]=1[C:8]#[N:9]

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 545931881-Aminocyclopentane-1-carboxamide hydrochloride

생성물 1

HCID 866661671-(6-Chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclopentanecarboxamide수율 49%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2,6-dichloro-3-cyano-5-fluoropyridine (250 mg, 1.30 mmol), 1-aminocyclopentanecarboxamide hydrochloride (214 mg, 1.30 mmol) and DIEA (0.650 mL, 3.73 mmol) in DMSO (3 mL) was stirred at 95 C for 4 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 50-100% EtOAc in hexane to give 1-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclopentanecarboxamide (180 mg).

후처리

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by a silica gel column
  5. washeluted with 50-100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-9b1b06fdd12d443bb23d15c821cf8101
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359375B2

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