Phthalic Anhydride → 2-({3-[2-(4-Fluorophenyl)-3-(methylcarbamoyl)-2H-indazol-6-yl]phenyl}carbamoyl)benzoic acid

HRID 1037565ノート

反応式

HRID 1037565 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[C:15]([CH:16]=2)=[N:14][N:13]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:12]=3[C:24]([NH:26][CH3:27])=[O:25])[CH:5]=[CH:6][CH:7]=1.[C:28]1(=[O:38])[O:33][C:31](=[O:32])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12>C(#N)C>[F:23][C:20]1[CH:21]=[CH:22][C:17]([N:13]2[C:12]([C:24](=[O:25])[NH:26][CH3:27])=[C:11]3[C:15]([CH:16]=[C:8]([C:4]4[CH:3]=[C:2]([NH:1][C:28]([C:29]5[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=5[C:31]([OH:33])=[O:32])=[O:38])[CH:7]=[CH:6][CH:5]=4)[CH:9]=[CH:10]3)=[N:14]2)=[CH:18][CH:19]=1

参加物

4

反応物 2

HCID 6811Phthalic AnhydrideHCID 569629266-(3-aminophenyl)-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide

生成物 1

HCID 692500272-({3-[2-(4-Fluorophenyl)-3-(methylcarbamoyl)-2H-indazol-6-yl]phenyl}carbamoyl)benzoic acid収率 55%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

To a solution of Compound (16) (10 mg, 0.03 mmol) in ACN (3 mL) was added phthalic anhydride (8.2 mg, 0.06 mmol) and the reaction mixture was heated to 70° C. and stirred for 15 h. The reaction mixture was then cooled to RT and the resulting precipitate was collected by filtration. The residue was washed with cold ACN (5 mL) to afford Compound (17) as an off-white amorphous solid (7.83 mg, 55%). ESI-MS m/z calculated for [M+H]+: 509.15; found: 509.08. 1H NMR (400 MHz, d6-DMSO) δ 13.07 (brs, 1H), 10.47 (s, 1H), 8.77-8.71 (m, 1H), 7.99-7.87 (m, 3H), 7.77-7.38 (m, 12H), 2.85 (d, J=4.5 Hz, 3H).

後処理

  1. temperatureThe reaction mixture was then cooled to RT
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThe residue was washed with cold ACN (5 mL)

出典と根拠

ORDレコード
ord-22fcd8d8baab48c899bd0180090912b8
出典データセット
uspto-grants-2013_10
特許番号
US08546389B2

反応ノート

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