Dichloromethane → HCID 178487954, compound

HRID 1422949Notes

Reaction equation

HRID 1422949 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-74477421adb44ff4b2b6215ad3589460
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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