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

HRID 1034864
ノート
印刷プレビュー

反応式

HRID 1034864 の反応式
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Cl:25])[C:9]=2[N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12]2)[NH:4][CH:3]=1.[C:26](Cl)(=[O:29])[CH2:27][CH3:28].[Li+].[OH-]>CN1C(=O)CCC1.C(Cl)Cl.O.N1C=CC=CC=1>[Cl:25][C:8]1[C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:12]2)=[C:10]2[C:2]([NH:1][C:26](=[O:29])[CH2:27][CH3:28])=[CH:3][NH:4][C:5]2=[N:6][CH:7]=1
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 3

HCID 3939Lithium HydroxideHCID 62324Propionyl chlorideHCID 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 67045346(R)-tert-butyl 1-(5-chloro-3-propionamido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate収率 63.6%

試薬・触媒・溶媒 4

HCID 962Water
溶媒
HCID 1049Pyridine溶媒
HCID 6344Dichloromethane溶媒2 回
HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

DCM (2 mL) and pyridine (1 mL) were added to (R)-tert-butyl 1-(3-amino-5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (0.3 g, 0.820 mmol; Example 91, Step A) in NMP (2 mL), and then propionyl chloride (0.228 g, 2.46 mmol) was added. The reaction was then stirred for 1 hour at room temperature, and then 3M aqueous LiOH (3 mL) was added. The reaction was stirred for 10 minutes. Water (10 mL) and DCM (10 mL) were then added, and the organic fraction was dried, filtered and concentrated. Purification of the crude product by reverse phase HPLC (5-95% ACN in water) gave the product (R)-tert-butyl 1-(5-chloro-3-propionamido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (0.220 g, 63.6% yield).

後処理

  1. stirringThe reaction was stirred for 10 minutes
  2. customthe organic fraction was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the crude product by reverse phase HPLC (5-95% ACN in water)

出典と根拠

ORDレコード
ord-87dd4493761a45e5ba17d0aa4030a9b9
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…

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