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

HRID 2076331ノート

反応式

HRID 2076331 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
45 °C

実験手順

(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+).

後処理

  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)

出典と根拠

ORDレコード
ord-23cbfb20da904816914a65e3eef78316
出典データセット
uspto-grants-2011_04
特許番号
US07923561B2

反応ノート

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