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

HRID 1509776Notes

Reaction equation

HRID 1509776 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 46233761HCID 46233761, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-923f23190ae6407c89cdc2d06b8fd668
Source dataset
uspto-grants-2012_07
Patent number
US08211402B2

Reaction notes

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