Dimethylformamide → 2-(4,6-Dimethoxy-2-triazinylamino)-2-(9-fluorenyl)acetic acid

HRID 2305372Notes

Reaction equation

[NH2:1][CH:2]([CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:3]([OH:5])=[O:4].[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[NH:24][N:23](Cl)[N:22]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>O.C(OCC)(=O)C>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[NH:24][N:23]([NH:1][CH:2]([CH:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]3[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:3]([OH:5])=[O:4])[N:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2.29 g (9.6 mmol) of 2-amino-2-(9-fluorenyl)acetic acid, 0.70 g (4.0 mmol) of 4,6-dimethoxy-2-chlorotriazine and 0.51 g (4.8 mmol) of sodium carbonate were introduced into a mixture of 16 ml of DMF and 16 ml of water and stirred at 80° C. for 13 hours. Then ethyl acetate and water were added and the phases were separated. The aqueous phase was acidified with 6 normal HCl and extracted three times with ethyl acetate. The organic phases were dried with MgSO4 and concentrated. The crude product was chromatographed on silica gel with ethyl acetate/n-heptane (1:1). 0.44 g (29.1%) of a white powder was obtained; RF=0.135, melting point 182-186° C.

Workup

customthe phases were separated
extractionextracted three times with ethyl acetate
dry with materialThe organic phases were dried with MgSO4
concentrationconcentrated
customThe crude product was chromatographed on silica gel with ethyl acetate/n-heptane (1:1)

Sources & evidence

ORD record: ord-1ec9a518fef24f69bb940d6171d03d1f
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06440975B1

Reaction notes

Loading…