Triethylamine → 3-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20543노트

반응식

HRID 20543 반응식
Cl[C:2]1[CH:29]=[C:28]([S:30]([N:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([O:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[CH:19]=1)[C:8]([NH:10][C:11]1[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=1)=[O:9].C(N(CC)CC)C>CO.C1COCC1.[Pd]>[CH3:35][N:33]([CH3:34])[S:30]([C:28]1[CH:29]=[CH:2][C:3]([O:4][C:5]2[CH:6]=[C:7]([CH:17]=[C:18]([O:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[CH:19]=2)[C:8]([NH:10][C:11]2[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=2)=[O:9])=[CH:26][CH:27]=1)(=[O:31])=[O:32]

참가 물질

6

반응물 2

HCID 8471TriethylamineHCID 115409373-{2-chloro-4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

생성물 1

HCID 115983163-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide수율 32.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-{2-chloro-4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (1.0 g, 1.9 mmol) in methanol (20 mL) and THF (20 mL) was added triethylamine (1.5 mL) and 10% palladium on carbon (100 mg). The resulting mixture was stirred under an atmosphere of hydrogen for 20 hours. The mixture was filtered through Celite® and evaporated under reduced pressure. The residue was dissolved in DCM (100 mL) and washed with 2M hydrochloric acid (100 mL). The organic phase was separated and the aqueous reextracted with DCM (100 mL). The combined organic extracts were dried (MgSO4) and evaporated to afford the title compound (300 mg, 32%).

후처리

  1. filtrationThe mixture was filtered through Celite®
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in DCM (100 mL)
  4. washwashed with 2M hydrochloric acid (100 mL)
  5. customThe organic phase was separated
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-dae1c8dce7914aeda10e9030581e2bb0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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