홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Citric Acid → (2S)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)-2-(1-(2-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide

HRID 1098011
노트
인쇄 미리보기

반응식

HRID 1098011 반응식
[H-].[Na+].[CH:3]1([O:7][CH2:8][C@H:9]([OH:20])[C:10]([NH:12][C:13]2[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=2)=[O:11])[CH2:6][CH2:5][CH2:4]1.Cl[C:22]1[N:27]=[CH:26][N:25]=[C:24]2[N:28]([C:31]3[C:32]([CH3:37])=[N:33][CH:34]=[CH:35][CH:36]=3)[N:29]=[CH:30][C:23]=12.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH:3]1([O:7][CH2:8][C@H:9]([O:20][C:22]2[N:27]=[CH:26][N:25]=[C:24]3[N:28]([C:31]4[C:32]([CH3:37])=[N:33][CH:34]=[CH:35][CH:36]=4)[N:29]=[CH:30][C:23]=23)[C:10]([NH:12][C:13]2[CH:18]=[N:17][C:16]([CH3:19])=[CH:15][N:14]=2)=[O:11])[CH2:6][CH2:5][CH2:4]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 575045064-chloro-1-(2-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine2회HCID 57504623HCID 57504623, 화합물

생성물 1

HCID 59279464(2S)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)-2-(1-(2-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide수율 41.6%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (19.54 mg, 0.49 mmol) was added to (S)-3-cyclobutoxy-2-hydroxy-N-(5-methylpyrazin-2-yl)propanamide (Intermediate R1) (102 mg, 0.41 mmol) in anhydrous THF (5 mL) at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 10 minutes and then 4-chloro-1-(2-methylpyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (Intermediate V5) (100 mg, 0.41 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was neutralised with 1M citric acid and the majority of the THF removed in vacuo. The reaction mixture was diluted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated and the aqueous layer re-extracted with ethyl acetate (2×50 mL). The combined organics were washed with saturated brine (25 mL), dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 5% MeOH in DCM to afford the product (78 mg, 41.6%). 1H NMR (400 MHz, DMSO) δ 1.23-1.36 (m, 1H), 1.38-1.51 (m, 1H), 1.60-1.75 (m, 2H), 1.96-2.07 (m, 2H), 2.13 (s, 3H), 2.27 (s, 3H), 3.71-3.87 (m, 2H), 3.89-3.98 (m, 1H), 5.71-5.78 (m, 1H), 7.28-7.34 (m, 1H), 7.75 (d, 1H), 8.15 (s, 1H), 8.39 (s, 1H), 8.45-8.51 (m, 2H), 8.93 (s, 1H), 11.01 (s, 1H), m/z (ESI+) (M+H)+=461.48; HPLC tR=1.75 min

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 hour
  3. customthe majority of the THF removed in vacuo
  4. additionThe reaction mixture was diluted with water (20 mL) and ethyl acetate (50 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer re-extracted with ethyl acetate (2×50 mL)
  7. washThe combined organics were washed with saturated brine (25 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe crude product was purified by flash silica chromatography
  11. washeluting with 0 to 5% MeOH in DCM

출처 및 근거

ORD 기록
ord-42787f34b76c4b0a8e2479458f0bc85a
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143263B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트