Dimethylformamide → 2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-3-carbonitrile

HRID 1189553노트

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HRID 1189553 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)(=[O:17])=[O:16].[CH3:23][N:24](C=O)C>C(#N)C>[CH3:7][C:5]1[NH:4][C:3]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:2]([CH3:1])[C:6]=1[C:23]#[N:24]

참가 물질

4

반응물 2

HCID 6228DimethylformamideHCID 583109223,5-dimethyl-2-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole

생성물 1

HCID 583109832,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-3-carbonitrile수율 83%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
25 °C

실험 절차

A mixture of 3,5-dimethyl-2-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole (576.0 mg, 1.809 mmol) and N-chlorosulfonylisocyanide (197 μl, 2.261 mmol) in acetonitrile (9.0 ml) was stirred at 25° C. for 1 hour. DMF (140 μl, 1.809 mmol) was then added and the resulting mixture was stirred for an additional 16 hours. It was quenched with water (100 ml) and extracted with dichloromethane (100 ml×2). The organic layers were combined, filtered, and evaporated to give an oil. The oil was purified by column chromatography (0 to 70% ethyl acetate in hexanes) to give 2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-3-carbonitrile (513.6 mg, 1.495 mmol, 83% yield) as brown oil. 1H NMR (CDCl3/400 MHz) δ (ppm) 9.10 (bs, 1H), 7.82-7.77 (m, 1H), 7.46-7.40 (m, 1H), 7.30-7.23 (m, 2H), 4.10 (s, 2H), 3.33-3.27 (m, 4H), 2.20 (s, 3H), 2.18 (s, 3H), 1.92-1.88 (m, 4H). MS m/z: 344.3 (M+1).

후처리

  1. stirringthe resulting mixture was stirred for an additional 16 hours
  2. customIt was quenched with water (100 ml)
  3. extractionextracted with dichloromethane (100 ml×2)
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil
  7. customThe oil was purified by column chromatography (0 to 70% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-e3ec5a4e907d4f1b830f23656e540c3c
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674115B2

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