Pyridine → HCID 25120679, compound

HRID 1924419Notes

Reaction equation

HRID 1924419 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1.[NH2:25][N:26]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[C:27]1[N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:25][N:26]2[C:35](=[O:36])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=[C:27]2[N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

8

Reactant 4

HCID 1049Pyridine2×HCID 65578Oxalyl chlorideHCID 1454243,5-Difluorophenylacetic acidHCID 67521418HCID 67521418, compound

Product 1

HCID 25120679HCID 25120679, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5-Difluorophenylacetic acid (0.227 g, 1.30 mmol) was dissolved in DCM (5 mL), followed by addition of oxalyl chloride (137 μL, 1.56 mmol) and 2 drops of dry DMF. After 1 hour gas evolution had stopped and pyridine (106 μL, 1.30 mmol) was added, followed by addition of 3-amino-2-pyrrolidin-1-yl-3H-quinazolin-4-one. After stirring at RT for 5 minutes additional pyridine (212 μL, 2.60 mmol) was added. The reaction mixture was stirred overnight at RT. The mixture was diluted with EtOAc (20 mL), washed with 1 M HCl (20 mL), dried (MgSO4) and evaporated in vacuo. The crude product was subjected to column chromatography (EtOAc/Heptane) giving the title compound (0.073 g, 15%). LC-ESI-HRMS of [M+H]+shows 385,1485 Da. Calc. 385,147607 Da.

Workup

  1. additionwas added
  2. washwashed with 1 M HCl (20 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c41cf8c6ff374dc4857fe0af7a2b8aaf
Source dataset
uspto-grants-2012_05
Patent number
US08178544B2

Reaction notes

Loading…