4-Fluoro-phenylsulfamoyl chloride → N-{2-[(1R)-2,3-dihydro-1H-inden-1-ylamino]quinolin-5-yl}-N'-(4-fluorophenyl)sulfamide

HRID 2076331노트

반응식

HRID 2076331 반응식
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([NH2:21])=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][S:30](Cl)(=[O:32])=[O:31])=[CH:25][CH:24]=1>N1C=CC=CC=1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:21][S:30]([NH:29][C:26]3[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=3)(=[O:31])=[O:32])[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 219665714-Fluoro-phenylsulfamoyl chlorideHCID 44219082(R)-N2-Indan-1-yl-quinoline-2,5-diamine

생성물 1

HCID 25019841N-{2-[(1R)-2,3-dihydro-1H-inden-1-ylamino]quinolin-5-yl}-N'-(4-fluorophenyl)sulfamide

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
45 °C

실험 절차

(R)—N2-Indan-1-yl-quinoline-2,5-diamine (example 43, step A+B, 200 mg, 0.727 mmol) was dissolved in 3 mL pyridine and 4-fluoro-phenylsulfamoyl chloride (298 mg, 1.42 mmol) was added. The reaction mixture was stirred at 45° C. for 2 days and quenched by addition of 50 mL water. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane, tetrahydrofurane 100:0->50:50 gradient). The title compound was obtained as a brown solid (43 mg, 13%), MS: m/e=449.1 (M+H+).

후처리

  1. customquenched by addition of 50 mL water
  2. extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (heptane, tetrahydrofurane 100:0->50:50 gradient)

출처 및 근거

ORD 기록
ord-23cbfb20da904816914a65e3eef78316
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923561B2

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