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Sodium Bicarbonate → 2-[(4-(5-Fluoro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl)methyl]-2,3-dihydro[1,4]dioxino[2,3-f]quinazoline

HRID 431013
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HRID 431013 반응식
[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][C@@H:2]1[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O)[N:11]=[CH:10][N:9]=[CH:8]3.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[C:37]1[CH2:38][CH2:39][NH:40][CH2:41][CH:42]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C1COCC1>[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[C:31]2[C:37]1[CH2:38][CH2:39][N:40]([CH2:15][CH:2]2[O:1][C:6]3=[C:7]4[C:12](=[CH:13][CH:14]=[C:5]3[O:4][CH2:3]2)[N:11]=[CH:10][N:9]=[CH:8]4)[CH2:41][CH:42]=1
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 113449595-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 12095706(2R)-2,3-Dihydro-1,4-dioxino[2,3-f]quinazolin-2-ylmethyl-4-methylbenzenesulfonate

생성물 1

HCID 101125952-[(4-(5-Fluoro-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl)methyl]-2,3-dihydro[1,4]dioxino[2,3-f]quinazoline

시약·촉매·용매 1

HCID 21974620
tetrahydrofuran N,N-dimethylformamide
용매

실험 절차

(2R)-2,3-Dihydro-1,4-dioxino[2,3-f]quinazolin-2-ylmethyl-4-methylbenzenesulfonate (800 mg, 3.7 mmole) was dissolved in a mixture of DMF/THF 1:1 v/v (30 mL) and 5-fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (800 mg, 4 mmole) added, followed by the addition of sodium bicarbonate (1.0 gm, 9.4 mmole) and the mixture was refluxed under nitrogen for 18 hours. The solvent was evaporated under vacuum and the residue partitioned between methylene chloride and water. The organic phase was separated, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and evaporated to a foam. Treatment of this foam with 3% methanol in chloroform yielded 320 mg (35%) of the (S)-enantiomer of the title compound as a yellow crystalline hemihydrate, m.p. 233-235° C.

후처리

  1. additionadded
  2. temperaturethe mixture was refluxed under nitrogen for 18 hours
  3. customThe solvent was evaporated under vacuum
  4. customthe residue partitioned between methylene chloride and water
  5. customThe organic phase was separated
  6. washwashed with water and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to a foam

출처 및 근거

ORD 기록
ord-217642dea49645f69afa9fd4fb7d5af4
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06656947B2

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