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

HRID 20543

反応式

HRID 20543 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-dae1c8dce7914aeda10e9030581e2bb0
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

関連ノート

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