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Triethylamine → N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide

HRID 2281250
ノート
印刷プレビュー

反応式

HRID 2281250 の反応式
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([OH:13])=O)[CH2:3]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]([NH2:48])([CH3:47])[CH3:46])=[CH:41][CH:40]=1.C(N(CC)CC)C>CN(C=O)C>[Br:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]([NH:48][C:11](=[O:13])[CH2:10][CH:4]2[CH:5]3[CH2:6][CH2:7][N:2]([CH2:9][CH2:8]3)[CH2:3]2)([CH3:46])[CH3:47])=[CH:43][CH:44]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 230091162-(4-Bromophenyl)propan-2-amineHCID 230241472-(Quinuclidin-3-yl)acetic acid hydrochloride

生成物 1

HCID 68327949N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide収率 76%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-(quinuclidin-3-yl)acetic acid hydrochloride (0.97 g, 4.7 mmol) in DMF (30 mL) was added HATU (1.79 g, 4.72 mmol), 2-(4-bromophenyl)propan-2-amine (1.0 g, 4.7 mmol), and triethylamine (3.9 mL, 28 mmol). The resulting mixture was stirred at 60° C. for 16 h. The mixture was concentrated in vacuo, diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4 and evaporated to afford crude product, which was purified by silica gel column chromatography (EtOAc/methanol 50/1 to 3/1) to obtain N-(2-(4-bromophenyl)propan-2-yl)-2-(quinuclidin-3-yl)acetamide as a yellow solid (1.3 g, 76%).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customto afford crude product, which
  7. customwas purified by silica gel column chromatography (EtOAc/methanol 50/1 to 3/1)

出典と根拠

ORDレコード
ord-15844f54be8346cc81bc8d0aaeb2204f
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09139580B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート