1-Methyl-2-imidazolecarboxaldehyde → HCID 46233761, compound

HRID 1509774Notes

Reaction equation

HRID 1509774 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.[CH3:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[CH:20]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])(=[O:39])[CH:37]=O>ClCCCl.CC(O)=O>[CH3:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[CH2:20][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)[CH2:37][C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]

Participants

7

Reactant 4

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 5049666Sodium triacetoxyborohydrideHCID 10986247Tert-butyl 2-oxoacetate

Product 1

HCID 46233761HCID 46233761, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(2-aminoethyl)benzenesulfonamide (1.40 g, 7.0 mmol), AcOH (0.30 mL) and 1-methyl-1H-imidazole-2-carboxaldehyde (0.77 g, 7.0 mmol) in DCE (40 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 (4.45 g, 21 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 then extracted with DCM and the organic layer was dried and concentrated under reduced pressure. The residue obtained was purified by flash chromatography over silica gel to tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 22%). 1H NMR (400 MHz, DMSO-d6) δ 7.65 (d, J=8.4 Hz, 2 H), 7.26 (s, 2 H), 7.21 (d, J=8.0 Hz, 2 H), 6.99 (d, J=0.8 Hz, 1 H), 6.73 (d, J=0.8 Hz, 1 H), 3.76 (s, 2 H), 3.38 (s, 3 H), 3.28 (s, 2 H), 2.79 (t, J=7.2 Hz, 2 H), 2.69 (t, J=6.8 Hz, 2 H), 1.40 (s, 9 H); ESMS m/z: 409 (M+H)+.

Workup

  1. customquenched with water
  2. extractionThe reaction mixture was then extracted with DCM
  3. customthe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by flash chromatography over silica gel to tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 22%)

Sources & evidence

ORD record
ord-6dc895a289b44da4beb4c5e2b23bb9e2
Source dataset
uspto-grants-2012_07
Patent number
US08211402B2

Reaction notes

Loading…