Triethylamine → 4-(3-Chloro-indazole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide

HRID 1178939

反応式

HRID 1178939 の反応式
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[F:11][C:12]1[CH:31]=[CH:30][C:15]([CH2:16][NH:17][C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:26]([C:23]2[CH:22]=[CH:21][C:20]([C:18]([NH:17][CH2:16][C:15]3[CH:30]=[CH:31][C:12]([F:11])=[CH:13][CH:14]=3)=[O:19])=[CH:25][CH:24]=2)(=[O:27])=[O:28])[N:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 958943-Chloro-1H-indazoleHCID 58975125HCID 58975125、化合物

生成物 1

HCID 589751524-(3-Chloro-indazole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Dissolve 3-chloro-1H-indazole (120 mg, 0.79 mmol) and 4-(4-fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (114 mg, 0.35 mmol) in CH2Cl2 (2.0 mL) and treat with Et3N (50 L, 0.36 mmol). Stir the solution for 1 h at RT, then dilute with additional CH2Cl2 (20.0 mL) and wash with satd aq. NaHCO3 (15 mL). Dry, filter, and concentrate the organic phase and purify the crude material by flash chromatography (100% hexanes to 50% EtOAc/hexanes linear gradient) to give the title compound (129 mg, 83%) as a white foam. MS (ES+) 443.9 (M+1)+, (ES−) 442.0 (M−1)−. 1H NMR (400 MHz, CDCl3): δ 8.17 (d, 1H, J=8.3), 8.03 (d, 2H, J=8.2), 7.83 (d, 2H, J=8.9), 7.64 (m, 2H), 7.41 (t, 1H, J=7.4), 7.27 (m, 2H), 7.01 (t, 2H, J=8.9), 6.31 (br s, 1H), 4.57 (d, 2H, J=5.9).

後処理

  1. washwash with satd aq. NaHCO3 (15 mL)
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate the organic phase
  5. custompurify the crude material by flash chromatography (100% hexanes to 50% EtOAc/hexanes linear gradient)

出典と根拠

ORDレコード
ord-33349d63e2504f7980b104abe6d22953
出典データセット
uspto-grants-2007_10
特許番号
US07276516B2

関連ノート

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