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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Triethylamine → 1-(3,3-Dimethyl-butyl)-piperidine-4-carboxylic Acid 2-methyl-4-(2-methyl-4,5-dihydro-1-oxa-3,6-diaza-benzo[e]azulene-6-carbonyl)-benzylamide

HRID 220985
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HRID 220985 반응식
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:21][CH2:20][C:19]3[N:18]=[C:17]([CH3:22])[O:16][C:15]=3[C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]2=3)=[O:11])=[CH:6][C:5]=1[CH3:27].C(N(CC)CC)C.[CH3:35][C:36]([CH3:49])([CH3:48])[CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][CH:42]([C:45](O)=[O:46])[CH2:41][CH2:40]1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:27][C:5]1[CH:6]=[C:7]([C:10]([N:12]2[CH2:21][CH2:20][C:19]3[N:18]=[C:17]([CH3:22])[O:16][C:15]=3[C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]2=3)=[O:11])[CH:8]=[CH:9][C:4]=1[CH2:3][NH:2][C:45]([CH:42]1[CH2:43][CH2:44][N:39]([CH2:38][CH2:37][C:36]([CH3:49])([CH3:48])[CH3:35])[CH2:40][CH2:41]1)=[O:46]
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 2733179PyBroPHCID 231123781-(3,3-Dimethylbutyl)piperidine-4-carboxylic acidHCID 67287214(4-Aminomethyl-3-methyl-phenyl)-(2-methyl-4,5-dihydro-1-oxa-3,6-diaza-benzo[e]azulen-6-yl)-methanone Hydrochloride

생성물 1

HCID 116423921-(3,3-Dimethyl-butyl)-piperidine-4-carboxylic Acid 2-methyl-4-(2-methyl-4,5-dihydro-1-oxa-3,6-diaza-benzo[e]azulene-6-carbonyl)-benzylamide
수율 69%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

(4-Aminomethyl-3-methyl-phenyl)-(2-methyl-4,5-dihydro-1-oxa-3,6-diaza-benzo[e]azulen-6-yl)-methanone hydrochloride from Example E119.2 (89 mg, 0.225 mmol) was dissolved in dichloromethane (10 ml) and triethylamine (to pH9) at room temperature. 1-(3,3-Dimethyl-butyl)-piperidine-4-carboxylic acid (53 mg, 0.25 mmol), DMAP (27 mg, 0.225 mmol) and PyBroP (165 mg, 0.36 mmol) were added and the mixture was heated at reflux for 18 h. The solution was diluted with EtOAc, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% dichloro-methane) to give a white solid identified as the title compound (84 mg, 69%).

후처리

  1. customat room temperature
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 18 h
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluant; 1% 35% ammonia:9% methanol:90% dichloro-methane)
  8. customto give a white solid

출처 및 근거

ORD 기록
ord-821226f5468f4ed8b752227fa022459e
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202858B2

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