Dimethylformamide → tert-Butyl 2-(3-(2,5-Dimethyl-1H-pyrrol-1-yl)-5-(methoxy(methyl)carbamoyl)-1H-pyrazol-1-yl)ethylcarbamate

HRID 1412002

反応式

HRID 1412002 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[C:11]([C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])[NH:10][N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.Cl[CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>O>[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[C:11]([C:13](=[O:14])[N:15]([O:17][CH3:18])[CH3:16])[N:10]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 3795708N-Boc-2-chloroethylamineHCID 866840463-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide

生成物 1

HCID 86684523tert-Butyl 2-(3-(2,5-Dimethyl-1H-pyrrol-1-yl)-5-(methoxy(methyl)carbamoyl)-1H-pyrazol-1-yl)ethylcarbamate収率 66%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

A 250-mL round-bottomed flask equipped with a magnetic stirrer was charged with 287c (10.4 g, 1.0 eq., 41.9 mmol), tert-butyl 2-chloroethylcarbamate (37.7 g, 5.0 eq., 210.0 mmol), Na2CO3 (22.3 g, 5.0 eq., 210.0 mmol), and DMF (100 mL). The reaction mixture was stirred at 110° C. overnight. After cooling to room temperature, the resulting mixture was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layer was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with ethyl acetate to afford 287d (10.8 g, 66%) as yellow oil. MS-ESI: [M+H]+ 392.0

後処理

  1. customA 250-mL round-bottomed flask equipped with a magnetic stirrer
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. concentrationThe combined organic layer was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica-gel column chromatography
  6. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-a97d1c1702154275b4ad7714984e7d7b
出典データセット
uspto-grants-2014_12
特許番号
US08921353B2

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