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

Diethyl Ether → 4-{2-Fluoro-4-[3-(2-phenylacetyl)thioureido]phenoxy}-2-[(pyrrolidin-1-yl)carbonylamino]pyridine

HRID 492777
노트
인쇄 미리보기

반응식

HRID 492777 반응식
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-:11][C:12]#[N:13].[K+].[NH2:15][C:16]1[CH:36]=[CH:35][C:19]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:29])[CH:22]=2)=[C:18]([F:37])[CH:17]=1.C(OCC)C>C(#N)C>[F:37][C:18]1[CH:17]=[C:16]([NH:15][C:12]([NH:13][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[S:11])[CH:36]=[CH:35][C:19]=1[O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34]2)=[O:29])[CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 7679Phenylacetyl chlorideHCID 516872Potassium thiocyanateHCID 231530584-(4-Amino-2-fluorophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine

생성물 1

HCID 576775874-{2-Fluoro-4-[3-(2-phenylacetyl)thioureido]phenoxy}-2-[(pyrrolidin-1-yl)carbonylamino]pyridine수율 34%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

2-Phenylacetyl chloride (100 mg) was dissolved in acetonitrile (2 ml) under a nitrogen atmosphere, and then potassium thiocyanate (126 mg) was added thereto at 50° C., followed by stirring at the same temperature for 1.5 hrs. A solution of 4-(4-amino-2-fluorophenoxy)-2-[(pyrrolidin-1-yl)carbonylamino]pyridine (41 mg) in acetonitrile (4 ml) was added thereto, followed by stirring at room temperature for 2.5 hr. The reaction mixture was cooled down to room temperature, and then partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:4). Fractions containing the target compound were concentrated to give a residue, to which a small amount of diethyl ether was added to precipitate crystals. A suspension containing the crystals was diluted with a small amount of hexane. The crystals were filtered off and dried under aeration to provide the titled compound (21.4 mg, 34%) as pale yellow crystals.

후처리

  1. customat 50° C.
  2. stirringby stirring at room temperature for 2.5 hr
  3. custompartitioned between ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:4)
  9. additionFractions containing the target compound
  10. concentrationwere concentrated
  11. customto give a residue
  12. customto precipitate crystals
  13. additionA suspension containing the crystals
  14. additionwas diluted with a small amount of hexane
  15. filtrationThe crystals were filtered off
  16. customdried under aeration

출처 및 근거

ORD 기록
ord-9bb397c451474c3f9717ce249a7a084f
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07531532B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트