Cesium carbonate → HCID 117843511, 화합물

HRID 2209065노트

반응식

HRID 2209065 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([O:17][C@@H:18]([C@H:20]3[CH2:24][NH:23][C:22](=[O:25])[CH2:21]3)[CH3:19])[C:14]3[NH:26][CH:27]=[N:28][C:13]=3[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([O-])([O-])=O.[Cs+].[Cs+].FC(F)(F)S(O[CH2:41][CH:42]([F:44])[F:43])(=O)=O>CN(C=O)C.CCOC(C)=O.O.[Cl-].[Na+].O>[F:43][CH:42]([F:44])[CH2:41][N:26]1[C:14]2[C:15]([O:17][C@@H:18]([C@H:20]3[CH2:24][NH:23][C:22](=[O:25])[CH2:21]3)[CH3:19])=[N:16][C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:12][C:13]=2[N:28]=[CH:27]1

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonate2회HCID 178488441HCID 178488441, 화합물

생성물 1

HCID 117843511HCID 117843511, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of crude (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.09 (ca. 0.13 mmol) in DMF (1 mL) was added Cs2CO3 (114 mg, 0.35 mmol) followed by 2,2-difluoroethyl trifluoromethanesulfonate (36 mg, 0.17 mmol). After 40 min, an additional portion of 2,2-difluoroethyl trifluoromethanesulfonate (7 mg, 0.03 mmol) was added. After an additional 30 min, the reaction mixture was diluted with EtOAc (20 mL), water (10 mL), and brine (10 mL). The phases were separated, and the aqueous phase was extracted with EtOAc (20 mL). The combined organic phase was dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography (0% to 10% MeOH in DCM) to afford (R)-4-((R)-1-(3-(2,2-difluoroethyl)-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.12.

후처리

  1. waitAfter an additional 30 min
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (20 mL)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography (0% to 10% MeOH in DCM)

출처 및 근거

ORD 기록
ord-d69e251246924c7ab1e51c3f359d78a8
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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