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

HRID 915598

반응식

HRID 915598 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8bb9175eff5f415988406bab711442fa
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265144B2

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