4-(2-Aminoethyl)benzenesulfonamide → HCID 46233761, 화합물

HRID 1509776노트

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HRID 1509776 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH:14]([C:16]1[N:17]([CH2:21]C(OC(C)(C)C)=O)[CH:18]=[CH:19][N:20]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:43]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])(=[O:46])[CH:44]=O>ClCCCl.CC(O)=O>[CH3:21][N:17]1[CH:18]=[CH:19][N:20]=[C:16]1[CH2:14][N:1]([CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:10](=[O:11])(=[O:12])[NH2:13])=[CH:8][CH:9]=1)[CH2:44][C:43]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46]

참가 물질

7

반응물 4

HCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 5049666Sodium triacetoxyborohydrideHCID 10986247Tert-butyl 2-oxoacetateHCID 58291458tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate

생성물 1

HCID 46233761HCID 46233761, 화합물수율 44.1%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매

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온도
0 °C

실험 절차

A solution of 4-(2-aminoethyl)benzenesulfonamide (0.70 g, 3.5 mmol), AcOH (0.20 mL) and tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0.735 g, 3.5 mmol) in DCE (20 mL) was heated at 80° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated sequentially with NaBH(OAc)3 (2.25 g, 10.5 mmol) and tert-butyl glyoxalate (1.80 g). The reaction mixture was stirred at room temperature overnight and quenched with water. The reaction mixture was extracted with DCM and the organic layer was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 35%). 1H NMR (400 MHz, DMSO-d6) δ 7.67 (d, J=8.4 Hz, 2H), 7.25 (s, 2H), 7.23 (d, J=8.4 Hz, 2H), 7.04 (d, J=1.2 Hz, 1H), 6.76 (d, J=1.2 Hz, 1H), 4.82 (s, 2H), 3.74 (s, 2H), 3.24 (s, 2H), 2.69-2.66 (m, 4H), 1.41 (s, 9H), 1.40 (s, 9H); ESMS m/z: 509 (M+H)+.

후처리

  1. customquenched with water
  2. extractionThe reaction mixture was extracted with DCM
  3. customthe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography over silica gel

출처 및 근거

ORD 기록
ord-923f23190ae6407c89cdc2d06b8fd668
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211402B2

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