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Diisopropanolamine → 6,11-dihydro-alpha-(1H-imidazol-2-yl)-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-methanol

HRID 324306
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인쇄 미리보기

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HRID 324306 반응식
CC(O)CNCC(O)C.C(OC(OCC)[N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)C.[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][C:45](=[C:48]3[C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=4[CH2:52][CH2:51][N:50]4[C:59]([CH:62]=[O:63])=[CH:60][N:61]=[C:49]34)[CH2:44][CH2:43]2)=[CH:36][CH:35]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(O)(=O)C>[NH:14]1[CH:18]=[CH:17][N:16]=[C:15]1[CH:62]([C:59]1[N:50]2[C:49]([C:48](=[C:45]3[CH2:44][CH2:43][N:42]([CH2:41][CH2:40][C:37]4[CH:38]=[CH:39][C:34]([O:33][CH2:32][C:23]5[CH:24]=[CH:25][C:26]6[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=6)[N:22]=5)=[CH:35][CH:36]=4)[CH2:47][CH2:46]3)[C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=3[CH2:52][CH2:51]2)=[N:61][CH:60]=1)[OH:63]
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참가 물질

7

반응물 4

HCID 8086DiisopropanolamineHCID 11430Potassium CarbonateHCID 38495351-(diethoxymethyl)-1H-imidazoleHCID 99156646,11-dihydro-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-carboxaldehyde

생성물 1

HCID 186125076,11-dihydro-alpha-(1H-imidazol-2-yl)-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-methanol
수율 98.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매3회

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온도
-78 °C

실험 절차

A mixture of diisopropanolamine (1.13 g) in THF was stirred under nitrogen at −78° C. N-Butillithium (2.5 M in hexanes, 4.3 ml) was added portionwise at −70° C. and the mixture was stirred for 15 minutes. 1-(Diethoxymethyl)-1H-imidazole (1.81 g) dissolved in THF was added dropwise at −70° C. and the mixture was stirred at −70° C. for 1 hour. Compound 4 (5.54 g) dissolved in THF was added dropwise at −70° C. and the mixture was stirred at −70° C. for 1 hour. The mixture was brought till room temperature and it was stirred at room temperature overnight. Acetic acid (5 ml) was added and the mixture was stirred at room temperature for 20 minutes. K2CO3 (5 g) was added and the mixture was evaporated. The residue was taken up in water and DCM and the layers were separated. The aqueous layer was extracted with DCM. The combined organic layers were dried, filtered off and the solvent was evaporated, yielding 6.1 g (97%) of 6,11-dihydro-α-(1H-imidazol-2-yl)-11-[1-[2-[4-(2-quinolinylmethoxy)phenyl]ethyl]-4-piperidinylidene]-5H-imidazo[2,1-b][3]benzazepine-3-methanol (compound 46).

후처리

  1. stirringthe mixture was stirred for 15 minutes
  2. additionwas added dropwise at −70° C.
  3. stirringthe mixture was stirred at −70° C. for 1 hour
  4. additionwas added dropwise at −70° C.
  5. stirringthe mixture was stirred at −70° C. for 1 hour
  6. customwas brought till room temperature
  7. stirringit was stirred at room temperature overnight
  8. stirringthe mixture was stirred at room temperature for 20 minutes
  9. customthe mixture was evaporated
  10. customDCM and the layers were separated
  11. extractionThe aqueous layer was extracted with DCM
  12. customThe combined organic layers were dried
  13. filtrationfiltered off
  14. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-65d5b82407a94af1ad601b0e84390d24
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06218381B1

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