Trifluoroacetic acid → 3-amino-3,4-dihydro-1,7-naphthyridin-2(1H)-one

HRID 1178448Notes

Reaction equation

HRID 1178448 reaction equation
ClC1SC2[NH:6][C:7]([C:9]([NH:11][CH:12]3[CH2:21][C:20]4[C:15](=CC=CC=4)[N:14](CC4NN=NN=4)[C:13]3=O)=[O:10])=[CH:8]C=2C=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:6][CH:7]1[CH2:8][C:21]2[C:12](=[CH:13][N:14]=[CH:15][CH:20]=2)[NH:11][C:9]1=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178521718HCID 178521718, compound

Product 1

HCID 219068393-amino-3,4-dihydro-1,7-naphthyridin-2(1H)-oneYield 319.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2-oxo-1,2,3,4-tetrahydro-1,7-naphthyridine-3-yl)carbamate (Method 29, 284 mg) was dissolved in DCM (10 mL) and treated with trifluoroacetic acid (5 mL). After stirring at ambient temperature for 1 hour the reaction mixture was evaporated under reduced pressure and the residue triturated with ether (20 mL), to give a light brown solid which was collected by filtration, washed with ether and dried to give the title compound (346 mg, 82%) as a bis trifluoracetate salt.

Workup

  1. customwas evaporated under reduced pressure
  2. customthe residue triturated with ether (20 mL)
  3. customto give a light brown solid which
  4. filtrationwas collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-6932d563733d4c0aa635ea120f5bc0d1
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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