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Sodium Hydroxide → 8-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid

HRID 2067032
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HRID 2067032 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[N:12][CH:13]=[C:7]2[C:6]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:24][CH2:23][CH2:22]2)=[CH:17][C:16]=1[F:25])=[O:4].[OH-].[Na+]>O.C(O)(=O)C>[CH:21]1([C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:6]3[C:7]4[N:8]([CH:11]=[N:12][CH:13]=4)[CH:9]=[CH:10][C:5]=3[C:3]([OH:4])=[O:2])=[C:16]([F:25])[CH:17]=2)[CH2:22][CH2:23][CH2:24]1
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 595652108-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester

생성물 1

HCID 595652038-(4-Cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid수율 102.9%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A suspension of 8-(4-cyclobutyl-2-fluoro-phenylamino)-imidazo[1,5-a]pyridine-7-carboxylic acid methyl ester (150 mg, 0.46 mmol) and 1M NaOH (1.5 mL, 1.5 mmol) in IMS (2 mL) was heated at 60° C. for 2 hours. The reaction mixture was then cooled to room temperature, diluted with water and glacial acetic acid was added to adjust pH to 4. The precipitate was filtered off and dried in a drying pistol at 40° C. for 18 hours to afford the title compound as a cream solid (154 mg, 99%). 1H NMR (DMSO-d6):10.53 (1 H, s), 8.34 (1 H, s), 7.74 (1 H, d, J=7.3 Hz), 7.35 (1 H, t, J=8.3 Hz), 7.24 (1 H, d, J=11.2 Hz), 7.13(1 H, d, J=8.1 Hz), 7.01 (1H, d, J=9.3 Hz), 6.23 (1H, s), 3.61 (1 H, m), 2.38 (2 H, m), 2.14 (2 H, m), 1.99 (1 H, m), 1.84 (1 H, m).

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. additionwas added
  3. filtrationThe precipitate was filtered off
  4. customdried in a drying pistol at 40° C. for 18 hours

출처 및 근거

ORD 기록
ord-df9576cb03bc417c95ec96e9ba311390
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08293763B2

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