1,2-Dichloroethane → HCID 59374187, 화합물

HRID 473753

반응식

HRID 473753 반응식
[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

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 59373922HCID 59373922, 화합물

생성물 1

HCID 59374187HCID 59374187, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e53b9dc0edcb4fcfb370536cba5092d0
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637500B2

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