Acetic Acid → HCID 58777639、化合物

HRID 1371739ノート

反応式

HRID 1371739 の反応式
[NH2:1][C:2]1[C:7]([C:8](=[O:18])[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31][O:32]C(=O)C)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1.[OH-].[K+].C(O)C.C(O)(=O)C>O>[NH2:1][C:2]1[C:7]([C:8]([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])=[O:18])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31][OH:32])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 58777653HCID 58777653、化合物

生成物 1

HCID 58777639HCID 58777639、化合物収率 52.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
25 °C

実験手順

A suspension of acetic acid 3-[4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonyl]-propyl ester (25 mg, 0.049 mmol, Example 274) in a solution of potassium hydroxide (50 mg, 0.9 mmol), water (1 mL) and ethanol (6 mL) was stirred at 25° C. for 1 hour. The solution was cooled, acidified with acetic acid and reduced in volume to 2 mL. This was diluted with water and the product extracted into methylene chloride. After washing with water, the organic layer was separated and dried (Na2SO4). The residue was purified by silica gel chromatography (ethyl acetate) and crystallized from methylene chloride/hexane to give [4-amino-2-[1-(3-hydroxy-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanoneas a white solid (12 mg, 50% yield). HRMS, observed: 468.1716; Calcd for (M+H)+: 468.1712

後処理

  1. temperatureThe solution was cooled
  2. extractionthe product extracted into methylene chloride
  3. washAfter washing with water
  4. customthe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customThe residue was purified by silica gel chromatography (ethyl acetate)
  7. customcrystallized from methylene chloride/hexane

出典と根拠

ORDレコード
ord-fed20fa9549441a791c3709d4fde659d
出典データセット
uspto-grants-2007_01
特許番号
US07157455B2

反応ノート

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