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

Ethanol → [8-(3,4-Difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-yl]-amine

HRID 451474
노트
인쇄 미리보기

반응식

HRID 451474 반응식
[CH3:1][C:2]1[O:6][C:5]([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)=[N:4][N:3]=1.[F:14][C:15]1[CH:16]=[C:17]([CH:22]2[CH2:27][CH2:26][CH2:25][N:24]3[N:28]=[C:29]([NH2:31])[N:30]=[C:23]23)[CH:18]=[CH:19][C:20]=1[F:21].C(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C.O>[F:14][C:15]1[CH:16]=[C:17]([CH:22]2[CH2:27][CH2:26][CH2:25][N:24]3[N:28]=[C:29]([NH:31][CH:10]4[CH2:11][CH2:12][N:7]([C:5]5[O:6][C:2]([CH3:1])=[N:3][N:4]=5)[CH2:8][CH2:9]4)[N:30]=[C:23]23)[CH:18]=[CH:19][C:20]=1[F:21]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 702EthanolHCID 4311764Sodium borohydride2회HCID 583978531-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-oneHCID 673426828-(3,4-Difluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine

생성물 1

HCID 58397875[8-(3,4-Difluoro-phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-yl]-amine

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A solution of 1-(5-methyl-1,3,4-oxadiazol-2-yl)piperidin-4-one (79.6 mg, 440 μmol) and 8-(3,4-difluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine (110 mg, 440 mmol) in toluene (5 mL) and acetic acid (280 μL) was heated to reflux at a Dean-Stark trap. The reaction mixture was cooled to room temperature and ethanol (3 mL) was added followed by sodium borohydride (66.5 mg, 61.9 μL, 1.76 mmol). The reaction mixture was stirred at 50° C. for 3 hours. Further sodium borohydride (66.5 mg, 61.9 μL, 1.76 mmol) was added and stirred at 50° C. for 3 hours. Water was added to the reaction mixture and the aqueous phase was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, 100 g, 0% to 15% MeOH in dichloromethane, 40 minutes). The title compound was obtained as a white solid (32.8 mg, 18%). MS ISP (m/e): 416.3 (69) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.16-7.07 (m, 1H), 7.00-6.93 (m, 1H), 6.91-6.87 (m, 1H), 4.12-4.01 (m, 4H), 3.93-3.87 (m, 2H), 3.72-3.60 (m, 1H), 3.23-3.13 (m, 2H), 2.38 (s, 3H), 2.32-2.23 (m, 1H), 2.18-1.88 (m, 5H), 1.58-1.48 (m, 2H).

후처리

  1. temperatureto reflux at a Dean-Stark trap
  2. stirringstirred at 50° C. for 3 hours
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography (silica gel, 100 g, 0% to 15% MeOH in dichloromethane, 40 minutes)

출처 및 근거

ORD 기록
ord-7e82613b6a2a4070813f87331fc4c022
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486967B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트