Trifluoroacetic acid → HCID 86715751, compound

HRID 627623Notes

Reaction equation

HRID 627623 reaction equation
COC1C=CC(C[NH:8][C:9]2[N:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)=CC=1.[C:21](O)(C(F)(F)F)=[O:22]>ClCCCl>[CH3:21][O:22][C:15]1[CH:16]=[N:17][C:18]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[N:10][C:9]=2[NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86715752HCID 86715752, compound

Product 1

HCID 86715751HCID 86715751, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of N-(4-methoxybenzyl)-1,7-naphthyridin-8-amine (340 mg, 1.15 mmol) in 1,2-dichloroethane (5.80 mL) was added TFA (2.67 mL, 34.5 mmol). The reaction was stirred at 75° C. for 8 hours and then concentrated. The residue was partitioned between DCM and aqueous sodium bicarbonate. The organic layer was concentrated and purified by silica-gel chromatography, eluting with 50-100% EtOAc in DCM, to provide the title compound (171.7 mg, 0.98 mmol) as an off-white solid. LC/MS (ESI+) m/z=176 (M+H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between DCM and aqueous sodium bicarbonate
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica-gel chromatography
  5. washeluting with 50-100% EtOAc in DCM

Sources & evidence

ORD record
ord-b5b8409d77294f948bcc20947c541ec4
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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