Acetic Acid → HCID 58777639, 화합물

HRID 1435318노트

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HRID 1435318 반응식
[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

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 58777653HCID 58777653, 화합물

생성물 1

HCID 58777639HCID 58777639, 화합물수율 52.4%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
25 °C

실험 절차

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)-methanone as a white solid (12 mg, 50% yield). HRMS, observed: 468.1716; Calcd for (M+H)+: 468.1712

후처리

  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

출처 및 근거

ORD 기록
ord-b7d52746de614d2da8390c521a595bab
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615634B2

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