Acetic Acid → HCID 22929440, compound

HRID 1828451Notes

Reaction equation

HRID 1828451 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(=O)C.CN(C)[CH:19]=[C:20]([C:26]1[N:27]=[N:28][N:29]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[N:30]=1)[C:21](OCC)=[O:22]>O>[CH3:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][N:29]2[N:28]=[N:27][C:26]([C:20]3[C:21](=[O:22])[N:12]4[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]4=[N:1][CH:19]=3)=[N:30]2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7015521Ethyl 2-aminopyridine-4-carboxylateHCID 53425728Ethyl 3-(dimethylamino)-2-{2-[(4-methoxyphenyl)methyl]-2H-tetrazol-5-yl}prop-2-enoate

Product 1

HCID 22929440HCID 22929440, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Ethyl 2-aminoisonicotinate (6.5 g, 39.23 mmol) was added with acetic acid (500 ml) and ethyl 3-(dimethylamino)-2-[2-(4-methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]-2-propenoate (13 g, 39.23 mmol) and refluxed by heating at 130° C. for 5 hours. The reaction solution was returned to room temperature and poured into water, and this was extracted with chloroform. The resulting organic layer was washed with saturated brine, and the collected organic layer was dried over magnesium sulfate. The organic layer was concentrated under reduced pressure and subjected to azeotropy with toluene, and the resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=80:1→50:1→30:1) to obtain 8.6 g of the title compound.

Workup

  1. temperaturerefluxed
  2. customwas returned to room temperature
  3. extractionthis was extracted with chloroform
  4. washThe resulting organic layer was washed with saturated brine
  5. dry with materialthe collected organic layer was dried over magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform→chloroform:methanol=80:1→50:1→30:1)

Sources & evidence

ORD record
ord-321b0188985a407aacfd83a3b18cafbb
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

Loading…