(R)-4-((R)-1-(3-(difluoromethyl)-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one → (R)-4-((R)-1-(3-(difluoromethyl)-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one

HRID 2209057노트

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HRID 2209057 반응식
[F:1][CH:2]([F:41])[N:3]1[C:7]2[C:8]([O:22][C@@H:23]([C@H:25]3[CH2:29][N:28]([C@@H](C4C=CC(OC)=CC=4)C)[C:27](=[O:40])[CH2:26]3)[CH3:24])=[N:9][C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)=[CH:11][C:6]=2[N:5]=[CH:4]1>C(O)(C(F)(F)F)=O>[F:41][CH:2]([F:1])[N:3]1[C:7]2[C:8]([O:22][C@@H:23]([C@H:25]3[CH2:29][NH:28][C:27](=[O:40])[CH2:26]3)[CH3:24])=[N:9][C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)=[CH:11][C:6]=2[N:5]=[CH:4]1

참가 물질

3

반응물 1

HCID 117843944(R)-4-((R)-1-(3-(difluoromethyl)-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

생성물 1

HCID 117843350(R)-4-((R)-1-(3-(difluoromethyl)-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
60 °C

실험 절차

(R)-4-((R)-1-(3-(difluoromethyl)-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 2.30 (max. 0.153 mmol) was dissolved in TFA (2 mL) and heated to 60° C. with stirring. After 22 h, the red solution was concentrated in vacuo and diluted with EtOAc (20 mL) and saturated aqueous NaHCO3 (20 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 onto 2 g silica gel. Purification by silica gel chromatography (0% to 2.5% to 5% MeOH in DCM) provided (R)-4-((R)-1-(3-(difluoromethyl)-6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.02.

후처리

  1. concentrationthe red solution was concentrated in vacuo
  2. additiondiluted with EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc (20 mL)
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated onto 2 g silica gel
  8. customPurification by silica gel chromatography (0% to 2.5% to 5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-830cbdbe8d5a44aca1ae03fb36c662d1
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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