Trifluoroacetic acid → HCID 117667425, compound

HRID 712615Notes

Reaction equation

HRID 712615 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2[CH:16]=[N:17][C:18]3[N:19]([C:25](=[O:27])[NH2:26])[CH2:20][CH2:21][CH2:22][C:23]=3[CH:24]=2)[CH:14]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:24]=[C:23]3[C:18](=[N:17][CH:16]=2)[N:19]([C:25]([NH2:26])=[O:27])[CH2:20][CH2:21][CH2:22]3)[CH:12]=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117672588HCID 117672588, compound

Product 1

HCID 117667425HCID 117667425, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[5-(8-Carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-ylmethyl]-carbamic acid tert-butyl ester (100 mg, 0.26 mmol) is dissolved in 5.0 mL of DCM and trifluoroacetic acid (0.5 mL) is added. The mixture is stirred for 1 hr and the solvent is removed in vacuo. The residue is dissolved in MeOH and filtered through a StratoSpheres SPE cartridge (PL-HCO3 MP SPE) to remove the acid. The filtrate is then concentrated to give 75 mg of 6-(5-aminomethyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide which is used in the next step without purification.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in MeOH
  3. filtrationfiltered through a StratoSpheres SPE cartridge (PL-HCO3 MP SPE)
  4. customto remove the acid
  5. concentrationThe filtrate is then concentrated

Sources & evidence

ORD record
ord-9e98b6dd688b41e28df03246d03f266e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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