3-(Methylthio)propionyl Chloride → HCID 59580749、化合物

HRID 533309ノート

反応式

HRID 533309 の反応式
[CH3:1][S:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[CH3:8][NH:9][C:10]1[S:14][C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:12][CH:11]=1>ClCCCl.CN(C1C=CN=CC=1)C>[CH3:8][N:9]([C:10]1[S:14][C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:12][CH:11]=1)[C:5](=[O:6])[CH2:4][CH2:3][S:2][CH3:1]

参加物

5

反応物 2

HCID 129214403-(Methylthio)propionyl ChlorideHCID 59580894N-methyl-2-(pyridin-3-yl)thiazol-5-amine

生成物 1

HCID 59580749HCID 59580749、化合物収率 75%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 111,2-Dichloroethane溶媒3 回

実験手順

A solution of 3-methylsulfanyl-propionyl chloride (120 mg, 0.9 mmol) in DCE (1 mL) was pipetted at a dropwise rate into an ice-cold suspension of methyl-(2-pyridin-3-yl-thiazol-5-yl)-amine (114 mg, 0.6 mmol) in DCE (5 mL), and the mixture was stirred for 5 min before adding a solution of DMAP (80 mg, 0.6 mmol) in DCE (1 mL). The ice bath was removed after 30 min, and the mixture was stirred at reflux under nitrogen for 15 min. The reaction mixture was cooled, diluted with DCE (70 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over MgSO4 and purified by silica gel chromatography (3:1 ethyl acetate/hexanes) to afford a fine yellow powder (131 mg, 75%): mp 116-118° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.08 (d, J=2.0 Hz, 1H), 8.61 (dd, J=4.8, 1.4 Hz, 1H), 8.24 (dt, J=9.8, 1.8 Hz, 1H), 7.81 (s, 1H), 7.51 (dd, J=7.7, 4.7 Hz, 1H), 3.56 (s, 3H), 3.02 (t, J=7.0 Hz, 2H), 2.76 (t, J=7.2 Hz, 2H), 2.12 (s, 3H); ESIMS m/z 294 (M+1).

後処理

  1. customThe ice bath was removed after 30 min
  2. stirringthe mixture was stirred
  3. temperatureat reflux under nitrogen for 15 min
  4. temperatureThe reaction mixture was cooled
  5. additiondiluted with DCE (70 mL)
  6. washwashed with saturated aqueous NaHCO3 (50 mL)
  7. dry with materialdried over MgSO4
  8. custompurified by silica gel chromatography (3:1 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-dd9e3bcb71c744238bda115d7ab27c5b
出典データセット
uspto-grants-2014_10
特許番号
US08853246B2

反応ノート

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