Nicotinic Acid → HCID 15680032, compound

HRID 703735Notes

Reaction equation

HRID 703735 reaction equation
[C:1]([O:7][C:8]1[CH:9]=[C:10]([CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27]Cl)=[O:25])[CH:11]=[CH:12][C:13]=1[O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:29]([OH:37])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1.C(N(CC)CC)C>CN(C)C=O>[N:32]1[CH:33]=[CH:34][CH:35]=[C:30]([C:29]([O:37][CH2:27][O:26][C:24]([NH:23][CH2:22][CH2:21][C:10]2[CH:11]=[CH:12][C:13]([O:14][C:15](=[O:20])[C:16]([CH3:17])([CH3:19])[CH3:18])=[C:8]([O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[CH:9]=2)=[O:25])=[O:36])[CH:31]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 15680031HCID 15680031, compound

Product 1

HCID 15680032HCID 15680032, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The chloromethyl carbamate prepared in Example 112 (1.26 g, 3.04 mmol) was combined with 10 mL of dry dimethylformamide and that mixture was added to a premixed solution of nicotinic acid (375 mg, 3.04 mmol) and triethylamine (445 mL, 5% excess) in 15 mL of dry dimethylformamide at room temperature. The reaction mixture was stirred for 4 days, then the precipitate which formed was removed by filtration. The filtrate was evaporated to dryness and the residue was taken up in 20 mL of methylene chloride. That solution was washed twice with 10 mL portions of water. Removal of the solvent in vacuo afforded the title compound of the formula: ##STR142## The identity of the product was confirmed by NMR.

Workup

  1. customthe precipitate which formed
  2. customwas removed by filtration
  3. customThe filtrate was evaporated to dryness
  4. washThat solution was washed twice with 10 mL portions of water
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-2e736adc90004dfcacbac79c4379223c
Source dataset
uspto-grants-1991_01
Patent number
US04983586

Reaction notes

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