Triethylamine → HCID 68278785, compound

HRID 1423271Notes

Reaction equation

HRID 1423271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([C:19](=[N:21][OH:22])[NH2:20])=[CH:14][CH:15]=3)[N:10]=[C:9]2[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:4][CH:3]=1.CCN(CC)CC.Cl.[N:39]1[CH:44]=[CH:43][C:42]([C:45](Cl)=O)=[CH:41][CH:40]=1>CN(C=O)C.CCOCC.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([C:19]4[N:20]=[C:45]([C:42]5[CH:43]=[CH:44][N:39]=[CH:40][CH:41]=5)[O:22][N:21]=4)=[CH:14][CH:15]=3)[N:10]=[C:9]2[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86692013HCID 86692013, compound

Product 1

HCID 68278785HCID 68278785, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a microwave vial containing methyl 5-[3-(4-fluorophenyl)-7-(N′-hydroxycarbamimidoyl)-4-oxo-3,4-dihydroquinazolin-2-yl]pentanoate (14B) in DMF was added Et3N (4 eq) and 4-pyridinecarbonyl chloride-HCl (1.2 eq). The mixture was stirred at rt for 1 h, then at 100° C. overnight. The mixture was then cooled to rt, diluted with Et2O, and saturated NaHCO3. The organic layer was separated, washed with H2O, brine, and dried over MgSO4. Concentration and purification by flash chromatography (EtOAc/hexanes) to afford methyl 5-(3-(4-fluorophenyl)-4-oxo-7-(5-(pyridin-4-yl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroquinazolin-2-yl)pentanoate.

Workup

  1. customat 100° C.
  2. customovernight
  3. temperatureThe mixture was then cooled to rt
  4. customThe organic layer was separated
  5. washwashed with H2O, brine
  6. dry with materialdried over MgSO4
  7. concentrationConcentration and purification by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-e12e9cea58a646f2aad43660a9aed7bd
Source dataset
uspto-grants-2015_01
Patent number
US08927559B2

Reaction notes

Loading…