Potassium Carbonate → 3-Amino-2-chloro-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine

HRID 1066769Notes

Reaction equation

HRID 1066769 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][N:8]([CH3:12])[CH2:9][C:10]=2[CH:11]=1.[Cl:13]N1C(=O)CCC1=O.CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.O.ClCCl>[NH2:1][C:2]1[C:3]([Cl:13])=[N:4][C:5]2[CH2:6][CH2:7][N:8]([CH3:12])[CH2:9][C:10]=2[CH:11]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 117449583-Amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine

Product 1

HCID 211964063-Amino-2-chloro-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-Amino-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine D4 (900 mg, 5.52 mmol) was dissolved in acetic acid (50 ml) before being treated portionwise with N-chlorosuccinimide (1.11 g, 8.28 mmol) 20 min. The reaction mixture was stirred overnight at room temperature under argon. The reaction mixture was diluted with water (125 ml), basified to pH10 with solid K2CO3 and extracted with dichloromethane (×2). The combined organic extracts were washed with sodium bicarbonate, dried (MgSO4) and evaporation in vacuo gave a crude black solid. Flash chromatography using dichloromethane (10% MeOH) gave thetitle compound as a pale orange solid.

Workup

  1. extractionextracted with dichloromethane (×2)
  2. washThe combined organic extracts were washed with sodium bicarbonate
  3. customdried
  4. custom(MgSO4) and evaporation in vacuo
  5. customgave a crude black solid
  6. customgave thetitle compound as a pale orange solid

Sources & evidence

ORD record
ord-d5c6bf76fcfc4e3797ab47b3513e3f4d
Source dataset
uspto-grants-2001_06
Patent number
US06245778B1

Reaction notes

Loading…