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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
ノート
印刷プレビュー

反応式

HRID 220985 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 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
収率 69%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-821226f5468f4ed8b752227fa022459e
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202858B2

反応ノート

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