Hydrochloric Acid → Tert-butyl 3-(5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate

HRID 2036958노트

반응식

HRID 2036958 반응식
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:5]2[N:22]=[CH:23][CH:24]=[C:4]2[N:3]=1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29].Cl.O1CCOCC1.[OH-].[Na+]>O.C(O)(C)(C)C>[Cl:25][C:26]1[CH:27]=[C:28]([NH:29][C:2]2[CH:7]=[C:6]([NH:8][C:9]3[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=3)[C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[N:5]3[N:22]=[CH:23][CH:24]=[C:4]3[N:3]=2)[CH:30]=[CH:31][CH:32]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 79323-ChloroanilineHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 58314667Tert-butyl 3-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate

생성물 1

HCID 58314302Tert-butyl 3-(5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate수율 55%

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

반응 조건

온도
100 °C

실험 절차

To the reaction flask, tert-butyl 3-(5-chloropyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate (2.9 g, 8.2 mmol) was added along with 3-chloroaniline (2.2 mL, 20.6 mmol), 4N HCl in dioxane (2.6 mL, 10.4 mmol), and t-butyl alcohol (41 mL). The reaction was stirred at 100° C. for 2 days then cooled to room temperature. The mixture was diluted with water, made basic with 3N NaOH, filtered and washed with water. The product, tert-butyl 3-(5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate, was collected as a solid in 55% yield after drying under vacuum overnight. LCMS (M+1=436)

후처리

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered
  3. washwashed with water
  4. customThe product, tert-butyl 3-(5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoate, was collected as a solid in 55% yield
  5. customafter drying under vacuum overnight

출처 및 근거

ORD 기록
ord-422ecdcd437b44e39253648f4e7f5078
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575177B2

반응 노트

불러오는 중…