2-Methylbenzenesulfonamide → 2-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxy-N-[(2-methylphenyl)sulfonyl]benzamide

HRID 915598

反応式

HRID 915598 の反応式
[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:14]=3[C:15](O)=[O:16])=[CH:10][C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:30]1([CH3:40])[C:31]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C.O>[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:14]=3[C:15]([NH:39][S:36]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH3:40])(=[O:37])=[O:38])=[O:16])=[CH:10][C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 69242-MethylbenzenesulfonamideHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 103400462-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxybenzoic acid

生成物 1

HCID 589586262-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxy-N-[(2-methylphenyl)sulfonyl]benzamide収率 10%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-[(1,3-diphenyl-1H-pyrazol-5-yl)amino]-5-methoxybenzoic acid (Example 29) (100 mg, 0.26 mmol) in dichloromethane (3 mL) were added o-toluenesulfonamide (53.3 mg, 0.31 mmol), EDCI (99.47 mg, 0.52 mmol), DMAP (63.40 mg, 0.52 mmol), and triethylamine (0.127 mL, 0.91 mmol). The reaction mixture was stirred for 2 h, and then diluted with dichloromethane (10 mL) and water (20 mL). The organic phase was separated and then washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography using 90% EtOAc/hexane, to afford the product (13.9 mg, 10.0%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.56 (s, 3H), 3.74 (s, 3H) 6.67 (s, 1H), 7.03 (dd, 2H), 7.26-7.60 (m, 14H), 7.84 (dd, 2H), 7.94 (d, 1H). ES-MS m/z 539.1 (MH+); HPLC RT (min) 3.71.

後処理

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-8bb9175eff5f415988406bab711442fa
出典データセット
uspto-grants-2007_09
特許番号
US07265144B2

関連ノート

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