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Triethylamine → (R)-tert-butyl 1-(5-chloro-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

HRID 1034835
ノート
印刷プレビュー

反応式

HRID 1034835 の反応式
C(N(CC)CC)C.[NH2:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([Cl:32])[C:16]=2[N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:19]2)[NH:11][CH:10]=1.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1.O[Li].O>CN1C(=O)CCC1.C(Cl)Cl.CO.CCOC(C)=O>[Cl:32][C:15]1[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:19]2)=[C:17]2[C:9]([NH:8][C:36]([CH:33]3[CH2:35][CH2:34]3)=[O:37])=[CH:10][NH:11][C:12]2=[N:13][CH:14]=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

8

反応物 4

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 67045610(R)-tert-butyl 1-(3-amino-5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

生成物 1

HCID 67045317(R)-tert-butyl 1-(5-chloro-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 21584119Ethylacetate methanol溶媒

反応条件

温度
0 °C

実験手順

Triethylamine (1018 μL, 7.462 mmol) was added to an aliquot of (R)-tert-butyl 1-(3-amino-5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (390 mg, 1.066 mmol; Example 91, Step A) in NMP (3 mL) at 0° C. under N2 atmosphere. The mixture was treated dropwise with cyclopropanecarbonyl chloride (580.4 μL, 6.396 mmol) and stirred at 0° C. for 1 hour. The reaction mixture was then diluted with CH2Cl2 (4 mL). 2M LiOH.H2O (9 mL) was added, and the mixture was allowed to stir for 24 hours. The mixture was then diluted with 2% MeOH/EtOAc (100 mL) and washed with water (4×20 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo. The residue obtained was purified by reverse phase chromatography (Biotage SP4, C-18 40M+, 15-85% CH3CN/water, 38 CV) to provide (R)-tert-butyl 1-(5-chloro-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate as a solid.

後処理

  1. stirringto stir for 24 hours
  2. washwashed with water (4×20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. customwas purified by reverse phase chromatography (Biotage SP4

出典と根拠

ORDレコード
ord-d8e5616c3b9c401a875f4b4e85354657
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08545897B2

反応ノート

読み込み中…

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