Trifluoroacetic acid → HCID 117667833, compound

HRID 712637Notes

Reaction equation

HRID 712637 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH2:24][O:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][CH2:24][C:22]2[CH:23]=[C:18]([C:14]3[CH:13]=[C:12]4[C:17](=[N:16][CH:15]=3)[NH:8][CH2:9][CH2:10][CH2:11]4)[CH:19]=[N:20][CH:21]=2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117667086HCID 117667086, compound

Product 1

HCID 117667833HCID 117667833, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[5-(4-Fluoro-phenoxymethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (42 mg, 0.096 mmol) is dissolved in 1.0 mL of DCM and trifluoroacetic acid (0.3 mL) is added. The mixture is stirred for 16 hrs and then the solvent is removed. The residue is dissolved in MeOH and filtered through Varian PL-HCO3 MP resin catridge to give 33 mg of 6-[5-(4-Fluoro-phenoxymethyl)-pyridin-3-yl]-1,2,3,4-tetrahydro-[1,8]naphthyridine which is used in the next step without purification.

Workup

  1. customthe solvent is removed
  2. dissolutionThe residue is dissolved in MeOH
  3. filtrationfiltered through Varian PL-HCO3 MP resin catridge

Sources & evidence

ORD record
ord-373143cfb11044c7ae41f1ae386bb834
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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