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

1,2-Dimethoxyethane → 5-[2-Methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine

HRID 908393
노트
인쇄 미리보기

반응식

HRID 908393 반응식
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[C:10]1[C:11]([NH2:25])=[N:12][CH:13]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:15]=1.Br[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)=[CH:29][C:28]=1[O:40][CH3:41].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:41][O:40][C:28]1[CH:29]=[C:30]([N:33]2[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]2)[CH:31]=[CH:32][C:27]=1[C:14]1[CH:15]=[C:10]([C:2]2[O:1][C:9]3[C:4]([N:3]=2)=[N:5][CH:6]=[CH:7][CH:8]=3)[C:11]([NH2:25])=[N:12][CH:13]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 673878191-(4-Bromo-3-methoxyphenyl)-4-methylpiperazineHCID 673889723-Oxazolo[4,5-b]pyridin-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

생성물 1

HCID 673881955-[2-Methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine수율 55.1%

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

Compound [6] was prepared as follows. 3-oxazolo[4,5-b]pyridin-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (138 mg), 1-(4-bromo-3-methoxy-phenyl)-4-methyl-piperazine (97 mg), bis(triphenylphosphine) palladium (II) chloride (50.1 mg) and sodium carbonate (50.5 mg) were weighed out and sealed in a tube. DME (3 ml) and water (0.3 ml) were added. Argon was bubbled in the resulting mixture for 10 minutes then it was stirred at 100° C. for 1 hour. After cooling, the reaction mixture was diluted with ethyl acetate (5 ml), filtered, and purified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane/ethyl acetate (1/1) then 5% methanolic ammonia 7N in dichloromethane/ethyl acetate (1/1). The solvent was evaporated to dryness and the product was triturated in acetonitrile (4 ml), collected by filtration, washed with Acetonitrile and dried under vacuum at 40° C., to give 5-[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (78 mg). NMR Spectrum: (CDCl3) 2.40 (s, 3H), 2.61-2.69 (m, 4H), 3.27-3.36 (m, 4H), 3.85 (s, 3H), 6.58 (d, 1H), 6.62 (dd, 1H), 6.91 (bs, 2H), 7.25 (d, 1H), 7.30 (dd, 1H), 7.85 (dd, 1H), 8.46 (d, 1H), 8.47 (d, 1H), 8.56 (dd, 1H); Mass spectrum: M+H+ 417. There was no deprotection step.

후처리

  1. customsealed in a tube
  2. customArgon was bubbled in the resulting mixture for 10 minutes
  3. temperatureAfter cooling
  4. additionthe reaction mixture was diluted with ethyl acetate (5 ml)
  5. filtrationfiltered
  6. custompurified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane/ethyl acetate (1/1)
  7. customThe solvent was evaporated to dryness
  8. customthe product was triturated in acetonitrile (4 ml)
  9. filtrationcollected by filtration
  10. washwashed with Acetonitrile
  11. customdried under vacuum at 40° C.

출처 및 근거

ORD 기록
ord-d85645e57dd440328183529ac49add56
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017611B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트