Sodium Hydroxide → 4-[2-(tert-Butoxycarbonylamino)ethylamino]-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxylic acid

HRID 333089ノート

反応式

HRID 333089 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][N:15]=[C:14]2[N:23]([CH3:27])[N:24]=[C:25]([CH3:26])[C:13]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Cl-].[NH4+]>CO.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=[C:14]2[N:23]([CH3:27])[N:24]=[C:25]([CH3:26])[C:13]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 86691173Ethyl 4-[2-(tert-butoxycarbonylamino)ethylamino]-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxylate

生成物 1

HCID 866911744-[2-(tert-Butoxycarbonylamino)ethylamino]-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxylic acid収率 826.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of ethyl 4-[2-(tert-butoxycarbonylamino)ethylamino]-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxylate (303 mg, 0.803 mmol) in methanol (30 ml) was added sodium hydroxide (4.02 g, 101 mmol) in water (10 ml) and the resulting mixture was heated at reflux for 1.5 hours. The mixture was allowed to cool to −50° C. after which ammonium chloride (6.07 g, 113 mmol) was added. The mixture was stirred at reflux for 15 minutes after which the solids were filtered off. The solids were washed with ethanol (150 ml) and the combined filtrates were concentrated under reduced pressure to yield 2.32 g of a white solid that was purified by filtration over a pad of silicagel in a glassfilter using 10% (1% AcOH in MeOH) in DCM. The filtrate was concentrated under reduced pressure to yield 240 mg (0.687 mmol, 86%). MS (ESI) m/z=350.2 [M+1]+.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. additionwas added
  4. temperatureat reflux for 15 minutes after which the solids
  5. filtrationwere filtered off
  6. washThe solids were washed with ethanol (150 ml)
  7. concentrationthe combined filtrates were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-ba45f4322a554c34b8d8c9024b2a97ea
出典データセット
uspto-grants-2014_11
特許番号
US08877934B2

反応ノート

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