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

HRID 737002

반응식

HRID 737002 반응식
[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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 958943-Chloro-1H-indazoleHCID 58975125HCID 58975125, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7d1af9b7d86a421cbcdeaaa5266986a4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595339B2

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