Hydrochloric Acid → 3-Amino-3,4-dihydro-1,5-naphthyridin-2(1h)-one dihydrochloride

HRID 1247530Notes

Reaction equation

HRID 1247530 reaction equation
[Cl:1]C1SC2[NH:6][C:7]([C:9]([NH:11][CH:12]3[CH2:21][C:20]4[C:15](=CC=CC=4)[N:14](CCOC)[C:13]3=O)=[O:10])=[CH:8]C=2C=1.[ClH:28]>C(Cl)Cl.O1CCOCC1>[ClH:1].[ClH:28].[NH2:6][CH:7]1[CH2:8][C:13]2[C:12](=[CH:21][CH:20]=[CH:15][N:14]=2)[NH:11][C:9]1=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 102506062-Chloro-N-{1-[2-(methoxy)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 219068583-Amino-3,4-dihydro-1,5-naphthyridin-2(1h)-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl(2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridine-3-yl)carbamate (Method 26, 263 mg, 1 mmol) was dissolved in DCM (10 mL) and treated with 4M HCl in dioxan (10 mL). After stirring at ambient temperature for 30 mins. the reaction mixture was evaporated under reduced pressure and the residue triturated with ether (20 mL), to give a white solid which was collected by filtration, washed with ether and dried. (234 mg, 100%).

Workup

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

Sources & evidence

ORD record
ord-86ba47d2b9b0499488c15133a5d70653
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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