Sodium Hydroxide → 4-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol

HRID 1360528ノート

反応式

HRID 1360528 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:34][CH2:35][CH3:36])[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:11]=[C:10]2[N:19](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.[OH-].[Na+]>Cl.C(O)C.CO>[NH2:19][C:10]1[C:9]2=[N:8][N:7]([CH2:34][CH2:35][CH3:36])[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:1])=[C:18]2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 66958564di(tert-butyl) 1-(4-hydroxybutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate

生成物 1

HCID 577175804-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol収率 27.6%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 887Methanol溶媒

実験手順

A solution of di(tert-butyl) 1-(4-hydroxybutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate (prepared as described in Parts A-C of Example 57, 0.507 g, 1.02 mmol) in 6 M HCl in ethanol (5 mL) was heated at 60° C. for 1.5 hours. The solution was allowed to cool to room temperature, and then was concentrated under reduced pressure to yield an oil. The oil was triturated with ether to obtain a solid that was isolated by filtration. The solid was dissolved in methanol and the solution was adjusted to approximately pH 14 with 50% aqueous sodium hydroxide. The solution was concentrated under reduced pressure and the crude product was purified by chromatography (silica gel, elution with 5% CMA in chloroform) followed by crystallization from hexanes/ethyl acetate to provide 0.084 g of 4-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butan-1-ol as white needles, mp 135.0-136.0° C.

後処理

  1. concentrationwas concentrated under reduced pressure
  2. customto yield an oil
  3. customThe oil was triturated with ether
  4. customto obtain a solid
  5. customthat was isolated by filtration
  6. concentrationThe solution was concentrated under reduced pressure
  7. customthe crude product was purified by chromatography (silica gel, elution with 5% CMA in chloroform)
  8. customfollowed by crystallization from hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-b857e44fcdb6417ea13ab5e7253213a5
出典データセット
uspto-grants-2011_02
特許番号
US07879849B2

反応ノート

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