Triethylamine → HCID 14698781, compound

HRID 1031937Notes

Reaction equation

HRID 1031937 reaction equation
O[C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.P(Cl)(Cl)([Cl:13])=O.[NH2:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]([CH3:28])[CH2:20][C:21]2([CH3:27])[CH3:26].C(N(CC)CC)C>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:13][C:2]1[C:3]([C:8]([NH:16][C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH:19]([CH3:28])[CH2:20][C:21]3([CH3:27])[CH3:26])=[O:10])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 112175411,1,3-Trimethylindan-4-amineHCID 178524895HCID 178524895, compound

Product 1

HCID 14698781HCID 14698781, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.5 g (3.57 mmols) of 3-hydroxypyrazine-2-carboxylic acid, 3 ml of phosphorus oxychloride, and one drop of pyridine was refluxed for 3 hours. The resultant reaction solution was distilled to remove excess phosphorus oxychloride. To the residue 5 ml of ethyl acetate was added. The solution was added dropwise to 10 ml of an ethyl acetate solution of 0.53 g (3 mmols) of 4-amino-1,1,3-trimethylindane and 0.4 g (3.96 mmols) of triethylamine. The resultant mixture was stirred at room temperature for 2 hours and then sequentially washed with water, sodium hydrogen carbonate, water, and a saturated brine. The washed solution was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/4), to obtain 0.58 g of light yellow crystals (Compound No. 10 shown in Table 5). The yield was 61%.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe resultant reaction solution
  3. distillationwas distilled
  4. customto remove excess phosphorus oxychloride
  5. additionTo the residue 5 ml of ethyl acetate was added
  6. washsequentially washed with water, sodium hydrogen carbonate, water
  7. dry with materialThe washed solution was dried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrated residue was separated
  10. custompurified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/4)

Sources & evidence

ORD record
ord-9e3e9d2de5ee463ca36a6d0ab246c3a8
Source dataset
uspto-grants-1990_09
Patent number
US04956375

Reaction notes

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