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

HRID 408378
ノート
印刷プレビュー

反応式

HRID 408378 の反応式
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([Br:30])[C:14]=2[N:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:17]2)[NH:9][CH:8]=1.[Li+].[OH-]>CN1C(=O)CCC1.C(Cl)Cl.O.N1C=CC=CC=1>[Br:30][C:13]1[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@@H:18]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:17]2)=[C:15]2[C:7]([NH:6][C:1](=[O:4])[CH2:2][CH3:3])=[CH:8][NH:9][C:10]2=[N:11][CH:12]=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 67045407(R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

生成物 1

HCID 67045151(R)-tert-butyl 1-(5-bromo-3-propionamido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate収率 52.8%

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), pyridine (0.5 mL) and propionyl chloride (0.180 g, 1.95 mmol) were added to (R)-tert-butyl 1-(3-amino-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (0.200 g, 0.487 mmol; Example 98, Step A) in NMP (3 mL). The reaction was then stirred for 1 hour at room temperature. 3M aqueous LiOH (3 mL) was then added, and 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 to give the crude product. Purification by reverse phase HPLC (5-95% ACN in water) gave the product (R)-tert-butyl 1-(5-bromo-3-propionamido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (0.120 g, 52.8% yield).

後処理

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

出典と根拠

ORDレコード
ord-d1c4df2edb934867a4ef660d82cd66f7
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08758830B2

反応ノート

読み込み中…

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