Dichloromethane → HCID 178487954, compound

HRID 2273237Notes

Reaction equation

HRID 2273237 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[N:17]=2)[N:12]=[CH:11][C:10]=1[NH2:21])C1C=CC=CC=1.ClCCl>[Pd].CO>[NH2:21][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:9]=1[OH:8])=[N:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 672542364-Benzyloxy-6-methoxy-[1,5]naphthyridin-3-ylamine

Product 1

HCID 178487954HCID 178487954, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

10% Palladium on activated carbon (76 mg, 0.07 mmol, 0.1 eq) is added at room temperature to a stirred solution of 4-benzyloxy-6-methoxy-[1,5]naphthyridin-3-ylamine (200 mg, 0.71 mmol, 1.0 eq) in methanol (20 mL). The resulting mixture is stirred under hydrogen flow (3 bars) at room temperature for 16 hours. The catalyst is then removed by filtration and the solution is concentrated to give a residue that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1 to 10:1, v/v) to afford 3-amino-6-methoxy-[1,5]naphthyridin-4-ol as a yellow solid (39 mg, 29% yield).

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe solution is concentrated
  3. customto give a residue that
  4. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-8afe5a57b7464442a9addcd2f0231ac4
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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