Water → N-[2-[[6-[(3S)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide

HRID 2353710

반응식

HRID 2353710 반응식
ClC1C=CC=C(C(OO)=O)C=1.[OH2:12].[Mn]([O-])(=O)(=O)=O.[Na+].[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][N:21]1[C:26]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:48])[NH:40][CH2:41][C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)=[CH:34][CH:33]=2)[N:29]=[C:28]([CH2:49][S:50][CH2:51][CH2:52][NH:53][C:54](=[O:56])[CH3:55])[CH:27]=1.[OH2:57]>O1CCOCC1>[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][N:21]1[C:26]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:48])[NH:40][CH2:41][C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)=[CH:34][CH:33]=2)[N:29]=[C:28]([CH2:49][S:50]([CH2:51][CH2:52][NH:53][C:54](=[O:56])[CH3:55])(=[O:57])=[O:12])[CH:27]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 70297m-Chloroperbenzoic acidHCID 516876Sodium permanganate monohydrateHCID 59380043N-[2-[[6-[(3S)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfanyl]ethyl]acetamide

생성물 1

HCID 59380059N-[2-[[6-[(3S)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

meta-Chloroperbenzoic acid (156 mg, 0.90 mmol) dissolved in Dioxane (2 mL), and sodium permanganate monohydrate (192 mg, 1.20 mmol) dissolved in water (1 mL) were added dropwise to N-[2-[[6-[(3S)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfanyl]ethyl]acetamide (162 mg, 0.30 mmol) in dioxane (6 mL) and water (2 mL) at RT under nitrogen. The resulting solution was stirred at RT for 1 hour. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol and pure fractions were evaporated to dryness. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents, to give the desired material as a white solid (61 mg).

후처리

  1. customThe crude product was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness
  4. customThe crude product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-7137156305b34f469a888bf9193aa96b
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750003B2

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