1,2-Dichloroethane → HCID 59374187、化合物

HRID 473753

反応式

HRID 473753 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:23]=[CH:22][C:11]([O:12][C:13]2[N:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=O)=[CH:10][CH:9]=1.Cl.[CH:25]1([CH2:28][NH2:29])[CH2:27][CH2:26]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH:25]1([CH2:28][NH:29][C:15](=[O:17])[C:14]2[CH:18]=[CH:19][CH:20]=[N:21][C:13]=2[O:12][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:23][CH:22]=2)[CH2:27][CH2:26]1

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 59373922HCID 59373922、化合物

生成物 1

HCID 59374187HCID 59374187、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a 100 mL round-bottomed flask was added 2-(4-(pyridin-2-ylamino)phenoxy)nicotinic acid (0.333 g, 1.08 mmol), cyclopropylmethanamine hydrochloride (0.116 g, 1.08 mmol), and TEA (0.4500 mL, 3.25 mmol) in DMF to stir for 5 min. EDC (0.2314 g, 1.19 mmol) and HOBT (0.1870 g, 1.19 mmol) was then added and allowed to stir overnight. The reaction mixture was diluted with water (10 mL) and extracted with DCM (3×10 mL). The organic extract was washed with water (1×10 mL), saturated sodium chloride (1×10 mL), saturated sodium bicarbonate (1×10 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (25M), eluting with a gradient of 1% to 5% methanol in DCM, to provide N-(cyclopropylmethyl)-2-(4-(pyridin-2-ylamino)phenoxy)nicotinamide. MS (ESI, pos. ion) m/z: 361.1 (M+1). IC50 (uM) 0.831.

後処理

  1. stirringto stir overnight
  2. extractionextracted with DCM (3×10 mL)
  3. extractionThe organic extract
  4. washwas washed with water (1×10 mL), saturated sodium chloride (1×10 mL), saturated sodium bicarbonate (1×10 mL)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed through a Biotage™ pre-packed silica gel column (25M)
  9. washeluting with a gradient of 1% to 5% methanol in DCM

出典と根拠

ORDレコード
ord-e53b9dc0edcb4fcfb370536cba5092d0
出典データセット
uspto-grants-2014_01
特許番号
US08637500B2

関連ノート

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