Acetic Acid → HCID 86692728, compound

HRID 1484610Notes

Reaction equation

HRID 1484610 reaction equation
[I:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CC(O)=O.[CH:26]([C:28]1[N:29]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:30]=[CH:31][N:32]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:26][C:28]2[N:29]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:30]=[CH:31][N:32]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16](=[O:17])(=[O:18])[NH2:19])=[CH:12][CH:11]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 58291458tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetateHCID 89677321HCID 89677321, compound

Product 1

HCID 86692728HCID 86692728, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2-((4-iodobenzyl)amino)ethyl)benzenesulfonamide (208 mg, 0.50 mmol), AcOH (0.05 mL) and tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0.105 mg, 0.50 mmol) in DCE (10 mL) at 0° C. was added NaBH(OAc)3 (0.30 g, 1.5 mmol). The reaction mixture was stirred at 0° C. for 30 minutes and at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by biotage over silica gel eluting with DCM to 10% MeOH in DCM to afford tert-butyl 2-(2-(((4-iodobenzyl)(4-sulfamoylphenethyl)amino)methyl)-1H-imidazol-1-yl)acetate (27.9 mg, 91%). 1H NMR (400 MHz, CDCl3) 7.78 (d, J=8.4 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 7.15 (d, J=8.4 Hz, 2H), 7.03 (d, J=8.0 Hz, 2H), 6.95 (d, J=1.2 Hz, 1H), 6.79 (d, J=0.8 Hz, 1H), 4.78 (s, 2H), 4.31 (s, 2H), 3.62 (s, 2H), 3.57 (s, 2H), 2.82-2.68 (m, 4H), 1.39 (s, 9H); MS (ESI), 611.1 (M+H)−.

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by biotage over silica gel eluting with DCM to 10% MeOH in DCM

Sources & evidence

ORD record
ord-f0b0b14a4ef94d32aece6ec2f5e111cf
Source dataset
uspto-grants-2016_08
Patent number
US09422251B2

Reaction notes

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