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

1,2-Dimethoxyethane → 1-[4-amino-2-(ethoxymethyl)-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol

HRID 598018
노트
인쇄 미리보기

반응식

HRID 598018 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.[F:25][C:26]1[N:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+].COCCOC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6]([C:29]3[CH:30]=[N:31][C:26]([F:25])=[CH:27][CH:28]=3)=[CH:5][C:4]=2[N:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 589706811-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol

생성물 1

HCID 589707161-[4-amino-2-(ethoxymethyl)-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol수율 36.4%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

A suspension of 1-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol (1.4 g, 3.55 mmol), 6-fluoropyridine-3-boronic acid (0.597 g, 4.26 mmol), potassium carbonate (1.62 g, 11.7 mmol), dichlorobis(triphenylphosphine)palladium(II)(0.025 g, 0.036 mmol), DME (13 mL), and water (7 mL) was stirred under a nitrogen atmosphere and then heated at 110° C. for 17.5 hours and allowed to cool to room temperature. The volatiles were removed under reduced pressure, and the residue was partitioned between water (25 mL) and dichloromethane (25 mL). A solid was present in the organic layer, and methanol was added to dissolve the solid. The aqueous layer was extracted with dichloromethane (3×20 mL). Silica gel was added to the combined organic fractions, and the mixture was concentrated under reduced pressure. The residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 5% to 15% methanol in ethyl acetate) followed by recrystallization from acetonitrile. The crystals were isolated by filtration, washed with acetonitrile, and dried in a vacuum oven to provide 530 mg of 1-[4-amino-2-(ethoxymethyl)-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol as white crystals, mp 218-220° C.

후처리

  1. temperatureto cool to room temperature
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between water (25 mL) and dichloromethane (25 mL)
  4. additionwas added
  5. dissolutionto dissolve the solid
  6. extractionThe aqueous layer was extracted with dichloromethane (3×20 mL)
  7. additionSilica gel was added to the combined organic fractions
  8. concentrationthe mixture was concentrated under reduced pressure
  9. customThe residue was purified by automated flash chromatography (40+M silica cartridge, eluting with 5% to 15% methanol in ethyl acetate)
  10. customfollowed by recrystallization from acetonitrile
  11. customThe crystals were isolated by filtration
  12. washwashed with acetonitrile
  13. customdried in a vacuum oven

출처 및 근거

ORD 기록
ord-1de03654983c4ee18c90c6b231155573
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07897609B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트