Thiophenol → HCID 56651603, 화합물

HRID 2369816노트

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HRID 2369816 반응식
[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

참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 66714522HCID 66714522, 화합물

생성물 1

HCID 56651603HCID 56651603, 화합물수율 43%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)]

후처리

  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

출처 및 근거

ORD 기록
ord-d2903218fb8349ee8e15bb9c668d7ade
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710044B2

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