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

Diisopropylethylamine → methyl 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

HRID 551810
노트
인쇄 미리보기

반응식

HRID 551810 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.[NH:36]1[CH2:40][CH2:39][CH:38]([C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)[CH2:37]1.C(=O)([O-])O.[Na+]>ClCCl>[N:43]1[CH:44]=[CH:45][CH:46]=[C:41]([CH:38]2[CH2:39][CH2:40][N:36]([C:28]([N:4]3[C:5]4[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:7][C:6]=4[O:1][CH2:2][CH2:3]3)=[O:34])[CH2:37]2)[CH:42]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 81531Diisopropylethylamine2회HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 16244461methyl 3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

생성물 1

HCID 67187798methyl 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate
수율 139.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1.8 g of methyl 3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate, 93.2 ml of dichloromethane and 4.62 ml of diisopropylethylamine are placed in a 250 ml round-bottomed flask under a nitrogen atmosphere. 1.38 g of triphosgene are added at 0° C. and then the reaction mixture is left stirring at ambient temperature for three hours. 1.62 ml of diisopropylethylamine and 1.45 g of 3-(pyrrolidin-3-yl)pyridine are subsequently added and the reaction mixture is stirred for eighteen hours. A saturated aqueous sodium hydrogencarbonate solution and dichloromethane are added. The aqueous phase is extracted three times with dichloromethane. The organic phases are combined, washed with water and with a saturated aqueous sodium chloride solution and dried over sodium sulfate and then the solvent is evaporated under reduced pressure. The residue is chroratographed on silica gel with a dichloromethane/methanol 95/5 mixture. 2.39 g of methyl 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate are obtained.

후처리

  1. waitthe reaction mixture is left
  2. stirringthe reaction mixture is stirred for eighteen hours
  3. extractionThe aqueous phase is extracted three times with dichloromethane
  4. washwashed with water and with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b6b04c9dcf1243518b52f82e1049480b
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947834B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트