Hydrochloric Acid → 2,2,2-Trifluoro-N-{3-[3-(2-{[3-(1,3-oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}acetamide

HRID 1157563

반응식

HRID 1157563 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:20]=[CH:21][CH:22]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[O:30]1[C:34]([C:35]2[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=2)[NH2:38])=[CH:33][N:32]=[CH:31]1.Cl>O1CCOCC1.CC(O)C>[F:26][C:25]([F:28])([F:27])[C:24]([NH:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:9]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:38][C:37]4[CH:39]=[CH:40][CH:41]=[C:35]([C:34]5[O:30][CH:31]=[N:32][CH:33]=5)[CH:36]=4)[N:7]=3)=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH:18]=1)=[O:29]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 27392893-(1,3-Oxazol-5-yl)anilineHCID 59513717N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide

생성물 1

HCID 577372422,2,2-Trifluoro-N-{3-[3-(2-{[3-(1,3-oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}acetamide수율 82.2%

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a solution of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (1.0 g, 0.002 mol) (see Example 1, Step C) in 1,4-dioxane (25 mL) and i-PrOH (5 mL) was added 3-(1,3-oxazol-5-yl)aniline (1.15 g, 0.007 mols) followed by catalytic 12M HCl. After heating overnight at 90° C., the reaction was quenched with saturated NaHCO3 (25 mL), the solvent was removed by rotary evaporation, the aqueous layer extracted with DCM (25 mL), the organic layer concentrated, and purified by column chromatography (5-50% EtOAc in hexanes then 100% EtOAc) to provide the product (0.89 g, 69%) as an off-white solid. ES-LC/MS m/z=542 [M+H]+.

후처리

  1. customthe reaction was quenched with saturated NaHCO3 (25 mL)
  2. customthe solvent was removed by rotary evaporation
  3. extractionthe aqueous layer extracted with DCM (25 mL)
  4. concentrationthe organic layer concentrated
  5. custompurified by column chromatography (5-50% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-28e1c21d1ba34714b8fe488dec9848b5
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807673B2

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