Allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate → Allyl trans-2-[3-(7-chloro-6-(4-chlorophenoxy)-quinazolin-4(3H)-on-3-yl)-2-oxopropyl]-3-methoxypiperidine-1-carboxylate

HRID 34615노트

반응식

HRID 34615 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.Br[CH2:22][C:23](=[O:39])[CH2:24][C@H:25]1[C@H:30]([O:31][CH3:32])[CH2:29][CH2:28][CH2:27][N:26]1[C:33]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34]>C[O-].[Na+].CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[N:7]([CH2:22][C:23](=[O:39])[CH2:24][C@H:25]3[C@H:30]([O:31][CH3:32])[CH2:29][CH2:28][CH2:27][N:26]3[C:33]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1

참가 물질

5

반응물 2

HCID 86741991Allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylateHCID 1357451607-chloro-6-(4-chlorophenoxy)quinazolin-4(3H)-one

생성물 1

HCID 86742318Allyl trans-2-[3-(7-chloro-6-(4-chlorophenoxy)-quinazolin-4(3H)-on-3-yl)-2-oxopropyl]-3-methoxypiperidine-1-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 10942334Sodium Methoxide용매

실험 절차

Under a nitrogen atmosphere in a flame-dried flask at room temperature and with magnetic stirring, 0.921 g (0.003 mol) of 7-chloro-6-(4-chlorophenoxy)quinazolin-4(3H)-one was slurried in 3.0 ml of 1.1N sodium methoxide. After 15 minutes, 1.00 g (0.003 mol) of allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate in 10 ml of methanol was added dropwise. After 2 hours, the reaction mixture was evaporated under reduced pressure, and the residue treated with water. The aqueous solution was extracted three times with 75 ml of dichloromethane. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated to afford the title compound: yield 1.28 g (76%); m.p. 138°-141° C. H-NMR(CDCl3) 1.3 to 1.9 (m, 4H), 2.6-3.4 (m, 6H), 3.3 (s, 3H), 4.9 (s, 2H), 4.5-6.2 (m, 5H), 7.1 (q, 4H), 7.6 (s, 1H), 7.8 (d, 2H) ppm.

후처리

  1. waitAfter 2 hours
  2. customthe reaction mixture was evaporated under reduced pressure
  3. additionthe residue treated with water
  4. extractionThe aqueous solution was extracted three times with 75 ml of dichloromethane
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-f42732280a2a465088300de1d708de3d
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762838

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