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Lithium hydroxide, monohydrate → 4-{5-[(1,4-diazabicyclo[2.2.2]oct-2-ylmethyl)amino]pyrazin-2-yl}-2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylic acid

HRID 655745
ノート
印刷プレビュー

反応式

HRID 655745 の反応式
[N:1]12[CH2:8][CH2:7][N:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:9][NH:10][C:11]1[N:12]=[CH:13][C:14]([C:17]2[N:18]=[C:19]([N:27]3[CH2:32][CH2:31][C@@H:30]([NH:33][C:34]([C:36]4[NH:37][C:38]([CH3:43])=[C:39]([Cl:42])[C:40]=4[Cl:41])=[O:35])[C@@H:29]([O:44][CH3:45])[CH2:28]3)[S:20][C:21]=2[C:22]([O:24]CC)=[O:23])=[N:15][CH:16]=1.O.[OH-].[Li+]>CO.O>[N:1]12[CH2:8][CH2:7][N:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:9][NH:10][C:11]1[N:12]=[CH:13][C:14]([C:17]2[N:18]=[C:19]([N:27]3[CH2:32][CH2:31][C@@H:30]([NH:33][C:34]([C:36]4[NH:37][C:38]([CH3:43])=[C:39]([Cl:42])[C:40]=4[Cl:41])=[O:35])[C@@H:29]([O:44][CH3:45])[CH2:28]3)[S:20][C:21]=2[C:22]([OH:24])=[O:23])=[N:15][CH:16]=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 168937Lithium hydroxide, monohydrateHCID 59402477ethyl 4-{5-[(1,4-diazabicyclo[2.2.2]oct-2-ylmethyl)amino]pyrazin-2-yl}-2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylate

生成物 1

HCID 594024554-{5-[(1,4-diazabicyclo[2.2.2]oct-2-ylmethyl)amino]pyrazin-2-yl}-2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylic acid収率 70.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Ethyl 4-{5-[(1,4-diazabicyclo[2.2.2]oct-2-ylmethyl)amino]pyrazin-2-yl}-2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylate (Example 194, 100 mg, 0.14 mmol) was dissolved in methanol (3 mL) and water (1 mL). Lithium hydroxide monohydrate (18 mg, 0.44 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The methanol was completely evaporated. The resulting crude product was taken in water (20 mL) and acidified to pH 6 with 2N hydrochloric acid (1.0 mL). The aqueous layer was concentrated to a residue, which was purified by preparative thin layer chromatography to afford 64 mg (66.8%) of 4-{5-[(1,4-diazabicyclo[2.2.2]oct-2-ylmethyl)amino]pyrazin-2-yl}-2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl]-1,3-thiazole-5-carboxylic acid as a light yellow solid.

後処理

  1. customThe methanol was completely evaporated
  2. concentrationThe aqueous layer was concentrated to a residue, which
  3. customwas purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-c3a1620d6bb8406fb6eeea424c9a9cec
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071605B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート