Dimethylformamide → HCID 57931404, compound

HRID 1669535Notes

Reaction equation

HRID 1669535 reaction equation
CN(C=O)C.[C:6]([NH:10][S:11]([C:14]1[C:15]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26]Br)=[CH:22][CH:21]=2)=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])([CH3:9])([CH3:8])[CH3:7].[CH2:28]([C:32]1[NH:36][C:35]([CH:37]=[O:38])=[C:34]([Cl:39])[N:33]=1)[CH2:29][CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O>[C:6]([NH:10][S:11]([C:14]1[C:15]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:36]3[C:35]([CH:37]=[O:38])=[C:34]([Cl:39])[N:33]=[C:32]3[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromideHCID 178418251HCID 178418251, compound

Product 1

HCID 57931404HCID 57931404, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a DMF (75 mL) solution of 4′-bromomethylbiphenyl-2-sulfonic acid t-butylamide (4.7 g, 12.2 mmol), was added 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde (2.3 g, 12.2 mmol) and potassium carbonate (1.7 g, 12.2 mmol). The mixture was stirred at room temperature overnight. EtOAc (400 mL) was added and the organic was washed 3 times with a sodium bicarbonate solution (200 mL) followed by saturated aqueous NaCl (200 mL). The solvent was removed and purification was achieved by silica gel chromatography (50/50 hexanes/EtOAc) using an isocratic gradient yielding intermediate (1a) as an off-white solid (5.0 g). Anal. HPLC: retention time=5.2 minutes. Gradient conditions: 10% solvent B/90% solvent A to 90% solvent B/10% solvent B over 6 minutes. MS m/z: [M+H]+ calcd for C25H30ClN3O3S, 488.18; found 488.6.

Workup

  1. washthe organic was washed 3 times with a sodium bicarbonate solution (200 mL)
  2. customThe solvent was removed
  3. custompurification

Sources & evidence

ORD record
ord-bf42bd84a8a84c54a3ba29a6e0d3fe1b
Source dataset
uspto-grants-2011_08
Patent number
US07989484B2

Reaction notes

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