Hydrochloric Acid → HCID 86710343, compound

HRID 1398345Notes

Reaction equation

HRID 1398345 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([NH:15]C(=O)O)[N:11]=[CH:12][CH:13]=3)[C:8](=[O:19])[N:7]([CH3:20])[C:6]=2[CH:21]=1.Cl.C(=O)(O)[O-].[Na+].[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>CO>[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29].[NH2:15][C:10]1[N:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[C:8](=[O:19])[N:7]([CH3:20])[C:6]1[CH:21]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86710342HCID 86710342, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 86710343HCID 86710343, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (8-chloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-4-yl)carbamic acid (300 mg, 0.415 mmol) in conc. HCl (15 mL, 494 mmol) was heated at 90° C. for 2 h. The pH of the reaction mixture was adjusted to 8 with saturated sodium bicarbonate solution and extracted with DCM (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by prep. HPLC (0.1% TFA in MeOH) to yield 4-amino-8-chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (30 mg, 0.110 mmol, 27% yield) as a mono TFA salt. LC/MS (ESI) m/e 260.0 [(M+H)+, calcd for C13H11ClN3O 260.05]; LC/MS retention time (method B): tR=1.18 min; HPLC retention time (method A): tR=5.24 min; HPLC retention time (method B): tR=6.31 min; 400 MHz, 1H NMR (DMSO-d6) δ 9.95 (s, 1H), 8.75 (s, 1H), 8.56 (d, J=8.80 Hz, 1H), 8.23 (d, J=6.80 Hz, 1H), 7.82 (dd, J=6.80, 7.20 Hz, 2H), 7.54 (dd, J=2.00, 8.80 Hz, 1H), 3.72 (s, 3H).

Workup

  1. extractionextracted with DCM (2×30 mL)
  2. washThe combined organic layers were washed with brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep

Sources & evidence

ORD record
ord-06cf9dc162644e22b657615df6b6230b
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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