3-Aminopyridine → HCID 117738793, compound

HRID 1506994Notes

Reaction equation

HRID 1506994 reaction equation
P([O-])(OC1C=CC=CC=1)OC1C=CC=CC=1.[NH2:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:19]=1[C:20]([OH:22])=O.[C:28]([O:32][C:33]([NH:35][C@@H:36]([CH3:40])[C:37](O)=O)=[O:34])([CH3:31])([CH3:30])[CH3:29].[NH2:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1>N1C=CC=CC=1.CCCCCC>[Cl:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:18]2[C:19]=1[C:20](=[O:22])[N:41]([C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1)[C:37]([C@@H:36]([NH:35][C:33](=[O:34])[O:32][C:28]([CH3:31])([CH3:30])[CH3:29])[CH3:40])=[N:17]2

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 750712-Amino-6-chlorobenzoic acidHCID 85082Tert-butoxycarbonylalanineHCID 23418553Diphenoxyphosphanolate

Product 1

HCID 117738793HCID 117738793, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent

Conditions

Temperature
40 °C

Procedure

Diphenyl phosphite (1.9 mL, 10 mmol) was added to a solution of 2-amino-6-chlorobenzoic acid (495 mg, 2.9 mmol) and (S)-2-(tert-butoxycarbonylamino)propanoic acid (710 mg, 3.77 mmol) in pyridine (3 mL). The reaction mixture was stirred at 40° C. for 2 hours. 3-Aminopyridine (274 mg, 3.48 mmol) was then added to the reaction mixture, which was then stirred at 55° C. for 12 hours. The reaction mixture was cooled to room temperature and loaded onto a hexane primed SiO2 column. The title compound was then purified by eluting with EtOAc in hexanes (0-50%) to afford (S)-tert-butyl 1-(5-chloro-4-oxo-3-(pyridin-3-yl)-3,4-dihydroquinazolin-2-yl)ethylcarbamate as a solid. ES/MS m/z=401.1 (M+H+).

Workup

  1. stirringwas then stirred at 55° C. for 12 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe title compound was then purified
  4. washby eluting with EtOAc in hexanes (0-50%)

Sources & evidence

ORD record
ord-0c4f45e547ea425fba5da555bdf2e6ff
Source dataset
uspto-grants-2015_12
Patent number
US09221795B2

Reaction notes

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