Triethylamine → HCID 13557454, compound

HRID 1583393Notes

Reaction equation

HRID 1583393 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[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[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][CH2:49][CH2:50][NH2:51])[CH:40]=1.C(N(CC)CC)C>CN(C)C=O.O.[OH-].[Na+]>[N:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][NH:51][C:18]([C:16]2[CH:15]=[CH:14][C:9]3[N:8]([CH:17]=2)[C:7](=[O:21])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=2)[N:10]=3)=[O:20])[CH:40]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 12562128HCID 12562128, compoundHCID 135574533-Pyridinehexanamine

Product 1

HCID 13557454HCID 13557454, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To an ice-cold suspension of 16.15 g of 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylic acid, 15.75 g of diphenylphosphorylazide, and 10.2 g of 6-(3-pyridyl)-hexanamine in 100 ml of dry dimethylformamide was added 8.0 ml of triethylamine. The reaction mixture was held at 0° C. for 2 hours and allowed to warm to room temperature over night. The resulting clear, yellow solution was diluted with water and 5M sodium hydroxide solution and was extracted with 3×300 ml of dichloromethane. The combined organic layers were dried over potassium carbonate and evaporated to a yellow semi-solid which was recrystallized from ethyl acetate-hexane to give 21.22 g (84%) of N-[6-(3-pyridyl)hexyl]-2-(1-methylethyl)-11-oxo-pyrido[2,1-b]-quinazoline-8-carboxamide, mp 94°-96° C. Recrystallization gave mp 100°-103° C. Conversion to the dihydrochloride salt gave 22.12 g, mp 230°-236° C. (dec.) and recrystallization from ethanol-ether gave 21.06 g, mp 234°-240° C. (dec.).

Workup

  1. extractionwas extracted with 3×300 ml of dichloromethane
  2. dry with materialThe combined organic layers were dried over potassium carbonate
  3. customevaporated to a yellow semi-solid which
  4. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ff16b840b351441a9c35eee00fb2d560
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

Loading…