Triethylamine → HCID 13557517, compound

HRID 1583405Notes

Reaction equation

HRID 1583405 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]1[C:14]([C:18]([OH:20])=O)=[CH:15][CH:16]=[CH:17][N:8]1[C:7]2=[O:21])[CH3:3].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][CH2:46][CH2:47][CH2:48][NH2:49])[CH:40]=1.C(N(CC)CC)C>CN(C)C=O.O>[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]1[C:14]([C:18]([NH:49][CH2:48][CH2:47][CH2:46][CH2:45][C:41]3[CH:40]=[N:39][CH:44]=[CH:43][CH:42]=3)=[O:20])=[CH:15][CH:16]=[CH:17][N:8]1[C:7]2=[O:21])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 72927Pyridine, 3-(4-aminobutyl)-HCID 199401P,P-Diphenylphosphinic azideHCID 13557514HCID 13557514, compound

Product 1

HCID 13557517HCID 13557517, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.82 g of 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carboxylic acid, 2.75 g of diphenylphosphoryl azide, and 1.50 g of 3-pyridinebutanamine in 30 ml of dry dimethylformamide was cooled in an ice bath as 1.0 g of triethylamine was added to the mixture. The reaction mixture was allowed to warm to room temperature over 18 hours, was diluted with water and was extracted with dichloromethane. The combined organic layer was washed with dilute sodium carbonate solution, dried over potassium carbonate and evaporated to dryness. The residue was crystallized repeatedly from ethyl acetate to give 0.25 g (6%) of 2-(1-methylethyl)-N-[4-(3-pyridinyl)butyl]-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carboxamide, mp 129°-130° C.

Workup

  1. additionwas added to the mixture
  2. extractionwas extracted with dichloromethane
  3. washThe combined organic layer was washed with dilute sodium carbonate solution
  4. dry with materialdried over potassium carbonate
  5. customevaporated to dryness
  6. customThe residue was crystallized repeatedly from ethyl acetate

Sources & evidence

ORD record
ord-15e46de16e604cc0a284aae7ddaaa8f0
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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