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Water → (S)-7-(1-Aminoethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one

HRID 515857
ノート
印刷プレビュー

反応式

HRID 515857 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[N:12]3[C:15]([CH3:18])=[CH:16][S:17][C:11]3=[N:10][C:9]=2[C@@H:19]([NH:21]C(=O)OC(C)(C)C)[CH3:20])[CH:5]=[CH:6][CH:7]=1.O1CCOCC1.O.[OH-].[Na+]>Cl>[NH2:21][C@H:19]([C:9]1[N:10]=[C:11]2[S:17][CH:16]=[C:15]([CH3:18])[N:12]2[C:13](=[O:14])[C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH3:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 58111443(S)-tert-butyl 1-(6-(3-fluorophenyl)-3-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidin-7-yl)ethylcarbamate

生成物 1

HCID 58111427(S)-7-(1-Aminoethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one収率 105.6%

試薬・触媒・溶媒 1

HCID 313
Hydrochloric Acid
溶媒

実験手順

(S)-tert-Butyl 1-(6-(3-fluorophenyl)-3-methyl-5-oxo-5H-thiazolo[3,2-a]pyrimidin-7-yl)ethylcarbamate (4.15 g, 10.3 mmol) was dissolved in a 4.0 M solution of hydrogen chloride in 1,4-dioxane (25.7 mL, 102.8 mmol) and the solution was stirred at room temperature for 45 minutes. HPLC indicated that the reaction was complete. To the solution was added water (10 mL) followed by 3 N aqueous sodium hydroxide solution at 0-5° C. to adjust the pH to 10. The aqueous mixture was extracted with ethyl acetate (2×30 mL). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give (S)-7-(1-Aminoethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one (3.30 g, 10.88 mmol, 103% yield). LCMS calculated for C15H15FN3OS (M+H)+: m/z 304.08; Found 303.9. 1H NMR (400 MHz, DMSO-d6) δ 8 7.45 (ddd, J=8.1, 7.9, 5.9 Hz, 1H), 7.19 (m, 1H), 7.12 (m, 2H) 7.04 (q, J=1.1 Hz, 1H), 3.57 (q, J=6.6 Hz, 1H), 2.64 (d, J=1.3 Hz, 3H), 1.10 (d, J=6.7 Hz, 3H)

後処理

  1. extractionThe aqueous mixture was extracted with ethyl acetate (2×30 mL)
  2. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-580cdf481c14444898a5a6b03554ae73
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108984B2

反応ノート

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