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Hydrochloric Acid → [1-(7-Cyclopropyl-6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethyl]-(9H-purin-6-yl)-amine

HRID 243370
ノート
印刷プレビュー

反応式

HRID 243370 の反応式
[CH:1]1([C:4]2[C:9]3[N:10]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:11]([C@@H:13]([NH:15][C:16]4[N:24]=[CH:23][N:22]=[C:21]5[C:17]=4[N:18]=[CH:19][N:20]5C4CCCCO4)[CH3:14])=[N:12][C:8]=3[CH:7]=[CH:6][C:5]=2[F:37])[CH2:3][CH2:2]1.Cl>CO.O1CCOCC1>[CH:1]1([C:4]2[C:9]3[N:10]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:11]([CH:13]([NH:15][C:16]4[N:24]=[CH:23][N:22]=[C:21]5[C:17]=4[N:18]=[CH:19][NH:20]5)[CH3:14])=[N:12][C:8]=3[CH:7]=[CH:6][C:5]=2[F:37])[CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 68158162[(S)-1-(7-Cyclopropyl-6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

生成物 1

HCID 178463569[1-(7-Cyclopropyl-6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)-ethyl]-(9H-purin-6-yl)-amine収率 48.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 31275
1,4-Dioxane
溶媒

実験手順

To a mixture of [(S)-1-(7-cyclopropyl-6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (20 mg, 0.04 mmol) in MeOH (2 mL) was added 4N HCl in dioxane (0.25 mL) and the reaction mixture stirred at RT for 30 min. The volatiles were removed under reduced pressure and the resulting residue purified by reverse phase HPLC (Phenomenex Gemini 5 μm C18 on a 20 min gradient 10-90%, 0.1% HCO2H in acetonitrile/water) to afford 198 (8 mg, 48%). LCMS (Method K): RT 3.74 and 3.81 min [M+H]+ 414.1. 1H NMR (DMSO-d6, 400 MHz): δ 12.89 (1H, br s), 8.19-7.97 (2H, m), 7.90-7.30 (7H, m), 7.04-6.95 (1H, dd, J=11.67, 8.76 Hz), 5.29 (1H, br s), 1.52 (3H, d, J=6.81 Hz), 1.28-1.18 (1H, m), 0.43-0.29 (2H, m), 0.25-0.08 (2H, m)

後処理

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting residue purified by reverse phase HPLC (Phenomenex Gemini 5 μm C18 on a 20 min gradient 10-90%, 0.1% HCO2H in acetonitrile/water)

出典と根拠

ORDレコード
ord-46ea6fefc83447c691df466030671e7f
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653089B2

反応ノート

読み込み中…

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