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Methanol → (S)-5-(1-(5-fluoro-2-methoxypyridin-3-yl)-2-hydroxyethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 1426958
ノート
印刷プレビュー

反応式

HRID 1426958 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][O:13]C(=O)[N:11]2[C:16]2[CH:21]=[CH:20][N:19]3[N:22]=[CH:23][C:24]([C:25]([O:27]CC)=[O:26])=[C:18]3[N:17]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.CO.C1COCC1.O.[OH-].[Li+]>O>[F:1][C:2]1[CH:3]=[C:4]([C@H:10]([NH:11][C:16]2[CH:21]=[CH:20][N:19]3[N:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[C:18]3[N:17]=2)[CH2:14][OH:13])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1
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 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86691742(S)-ethyl 5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

生成物 1

HCID 86691743(S)-5-(1-(5-fluoro-2-methoxypyridin-3-yl)-2-hydroxyethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid収率 45.2%

試薬・触媒・溶媒

1
HCID 962Water溶媒

実験手順

To a solution of (S)-ethyl 5-(4-(5-fluoro-2-methoxypyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (311 mg, 0.77 mmol) in a 1:1:1 mixture of MeOH:THF:H2O (15 mL) was added lithium hydroxide monohydrate (97.6 mg, 2.32 mmol). The mixture was stirred at ambient temperature for 16 hours and then at 50° C. for 19 hours, then concentrated to ⅓ volume, diluted with water (30 mL) and acidified to pH 4-5 with 1N HCl. The resulting precipitate was collected by filtration, washed with water and Et2O then dried under reduced pressure to afford (S)-5-(1-(5-fluoro-2-methoxypyridin-3-yl)-2-hydroxyethylamino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (121 mg, 45% yield) as a white powder. MS (apci) m/z=347.9 (M+H).

後処理

  1. waitat 50° C. for 19 hours
  2. concentrationconcentrated
  3. additiondiluted with water (30 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water and Et2O
  6. customthen dried under reduced pressure

出典と根拠

ORDレコード
ord-954b8a45a5354b75b6150a37770b7453
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933084B2

反応ノート

読み込み中…

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