Triethylamine → HCID 44211255, compound

HRID 1720878Notes

Reaction equation

HRID 1720878 reaction equation
[N:1]1[CH:6]=[C:5](C(O)=O)[CH:4]=[N:3][CH:2]=1.[NH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[CH:15]=[CH:14]2.C([N:23]([CH2:26]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1>O1CCOCC1>[CH3:20][N:16]1[C:17]2[C:13](=[CH:12][C:11]([NH:10][C:26]([NH:23][C:5]3[CH:4]=[N:3][CH:2]=[N:1][CH:6]=3)=[O:35])=[CH:19][CH:18]=2)[CH:14]=[CH:15]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78346Pyrimidine-5-carboxylic acidHCID 199401P,P-Diphenylphosphinic azideHCID 27695641-methyl-1H-indol-5-amine

Product 1

HCID 44211255HCID 44211255, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of acid (D4, 1.22 g, 9.8 mmol), 5-amino-1-methyl indole (D2, 1.43 g, 9.8 mmol), triethylamine (1.4 ml) and diphenylphosphoryl azide (2.1 ml, 10 mmol) in 1,4-dioxan (100 ml) was heated under reflux overnight. The mixture was evaporated and the residue was dissolved in dichloromethane and washed with 5% citric acid, sat. sodium bicarbonate and water. The organic phase was dried and evaporated and the residue was chromatographed on silica (100 g) eluted with 2-15% methanol/dichloromethane. Combination of appropriate fractions followed by recrystallisation from dichloromethane/methanol gave pure (E3, 0.70 g). mp 210°-213° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe mixture was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with 5% citric acid, sat. sodium bicarbonate and water
  6. customThe organic phase was dried
  7. customevaporated
  8. customthe residue was chromatographed on silica (100 g)
  9. washeluted with 2-15% methanol/dichloromethane
  10. customCombination of appropriate fractions followed by recrystallisation from dichloromethane/methanol

Sources & evidence

ORD record
ord-07ad94556b684ded85bb995271d530b5
Source dataset
uspto-grants-1996_04
Patent number
US05508288

Reaction notes

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