Thiophenol → HCID 56651603、化合物

HRID 2369816ノート

反応式

HRID 2369816 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:24][C:25]2[C:34]3[C:29](=[C:30]([C:35]([NH2:37])=[O:36])[CH:31]=[CH:32][CH:33]=3)[N:28]=[C:27]([CH3:38])[N:26]=2)[CH2:9][N:10]([CH3:23])S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(S)C=CC=CC=1>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:24][C:25]2[C:34]3[C:29](=[C:30]([C:35]([NH2:37])=[O:36])[CH:31]=[CH:32][CH:33]=3)[N:28]=[C:27]([CH3:38])[N:26]=2)[CH2:9][NH:10][CH3:23])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 66714522HCID 66714522、化合物

生成物 1

HCID 56651603HCID 56651603、化合物収率 43%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Crude 4-[((1S)-1-(4-Fluorophenyl)-2-{methyl[(4-nitrophenyl)sulfonyl]amino}ethyl)-amino]-2-methylquinazoline-8-carboxamide (161 mg; 0.30 mmol) and Cs2CO3 (488 mg; 1.50 mmol) were suspended in CH3CN (7 ml), and stirred for 10 minutes at room temperature. Benzenethiol (0.12 ml; 1.20 mmol) was added via syringe and the solution was stirred vigorously at room temperature overnight. The reaction mixture was concentrated, dissolved in DMSO (3 ml), and purified via Reverse Phase chromatography (Yamazen, basic buffer) to provide 9 16? (46 mg; 43% yield) as the free base. LC-MS [354 (M+1)]

後処理

  1. stirringthe solution was stirred vigorously at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in DMSO (3 ml)
  4. custompurified via Reverse Phase chromatography (Yamazen, basic buffer)
  5. customto provide 9 16

出典と根拠

ORDレコード
ord-d2903218fb8349ee8e15bb9c668d7ade
出典データセット
uspto-grants-2014_04
特許番号
US08710044B2

反応ノート

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