Sodium Bicarbonate → HCID 60003419, compound

HRID 2181685Notes

Reaction equation

HRID 2181685 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]3[O:19][CH:18]=[C:17]([C:20]#[C:21][Si](C)(C)C)[C:16]=3[CH:26]=1)=[O:11])[CH2:2]2.C([O-])(O)=O.[Na+]>CO>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]3[O:19][CH:18]=[C:17]([C:20]#[CH:21])[C:16]=3[CH:26]=1)=[O:11])[CH2:2]2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 69794947HCID 69794947, compound

Product 1

HCID 60003419HCID 60003419, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-3-[(trimethylsilyl)ethynyl]-1-benzofuran-5-carboxamide (255 mg, 0.70 mmol) is dissolved in MeOH (6 ml). The solution is treated with saturated NaHCO3 (2 ml) and the reaction is stirred overnight at RT. The volatiles are removed in vacuo and the residue is chromatographed over 30 g silica gel (230-400 mesh) eluting with 8% MeOH/CHCl3+1% conc. NH4OH. The appropriate fractions are combined and concentrated to give 190 mg of a yellow foam. The foam is crystallized from Et2O to provide 138 mg (67%) of Example 22 as a pale yellow solid. HRMS (ESI) calcd for C18H18N2O2+H: 295.1446, found 295.1458 (M+H)+.

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is chromatographed over 30 g silica gel (230-400 mesh)
  3. washeluting with 8% MeOH/CHCl3+1% conc. NH4OH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2738f9828b544b0dacf8939ffdcc7cd7
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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