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Diisopropylethylamine → methyl 2-{8-chloro-2-[N-(3-(1,2,3,4-tetrahydropyridino[2,3-b]pyridin-7-yl)propyl)carbamoyl]-1H,3H,4H,5H-benzo[e]azepin-5-yl}acetate

HRID 1057514
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인쇄 미리보기

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HRID 1057514 반응식
[ClH:1].[C:2]([O:5][CH2:6]C)(=[O:4])[CH3:3].[C:8](Cl)(Cl)=[O:9].[C:12]1(C)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH:19]1[C:24]2=[N:25][C:26]([CH2:29][CH2:30][CH2:31][NH2:32])=[CH:27][CH:28]=[C:23]2[CH2:22][CH2:21][CH2:20]1.C([N:36]([CH2:40][CH3:41])[CH:37]([CH3:39])C)(C)C>>[Cl:1][C:17]1[CH:12]=[CH:13][C:14]2[CH:15]([CH2:3][C:2]([O:5][CH3:6])=[O:4])[CH2:41][CH2:40][N:36]([C:8](=[O:9])[NH:32][CH2:31][CH2:30][CH2:29][C:26]3[N:25]=[C:24]4[NH:19][CH2:20][CH2:21][CH2:22][C:23]4=[CH:28][CH:27]=3)[CH2:37][C:39]=2[CH:16]=1
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참가 물질

5

반응물 4

HCID 81531DiisopropylethylamineHCID 98775993-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amineHCID 19083224Phosgen tolueneHCID 21866389Hydrogen chloride-ethyl acetate

생성물 1

HCID 69157953methyl 2-{8-chloro-2-[N-(3-(1,2,3,4-tetrahydropyridino[2,3-b]pyridin-7-yl)propyl)carbamoyl]-1H,3H,4H,5H-benzo[e]azepin-5-yl}acetate

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온도
50 °C

실험 절차

A solution of methyl 2-{2-[(tert-butyl)oxycarbonyl-8-chloro-1H,3H,4H,5H-benzo[e]azepin-5-yl}acetate (1 eq) in 1.17 M of HCl/ethyl acetate (30 eq) was stirred at room temperature for 18 hr. The reaction mixture was concentrated and dried under vacuum oven. The resulting residue was dissolved in methylene chloride (0.15 M) and followed by the addition of phosgene/toluene (20%) (10 eq) under nitrogen. After stirring for 1 hr, the solvent was removed by rotary evaporation. The residue was dissolved in 1 ml of N,N-dimethylformamide (0.07 M), followed by the addition of 3-(1,2,3,4-tetrahydropyridino[2,3-b]pyridin-7-yl)propylamine (2 eq) and N,N-diisopropylethylamine (10 eq). The reaction mixture was heated at 50° C. for 2 hr. The reaction solvent was removed by rotary evaporation and the residue was purified by flash chromatography (5% methanol/methylene chloride. EI-MS m/z 471 (M+H)+.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customdried under vacuum oven
  3. dissolutionThe resulting residue was dissolved in methylene chloride (0.15 M)
  4. customthe solvent was removed by rotary evaporation
  5. dissolutionThe residue was dissolved in 1 ml of N,N-dimethylformamide (0.07 M)
  6. customThe reaction solvent was removed by rotary evaporation
  7. customthe residue was purified by flash chromatography (5% methanol/methylene chloride

출처 및 근거

ORD 기록
ord-72527742638549a38e123850f576bf01
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06514964B1

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