Trifluoroacetic acid → HCID 117667286, compound

HRID 712735Notes

Reaction equation

HRID 712735 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][N:25]([CH3:34])[C:26]([CH:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:27])[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>[CH3:34][N:25]([CH2:24][C:22]1[CH:21]=[N:20][CH:19]=[C:18]([C:14]2[CH:15]=[N:16][C:17]3[NH:8][CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=2)[CH:23]=1)[C:26]([CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[O:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117667526HCID 117667526, compound

Product 1

HCID 117667286HCID 117667286, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(5-{[Methyl-(tetrahydro-pyran-4-carbonyl)-amino]-methyl}-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (70 mg, 0.15 mmol) is dissolved in DCM (2.0 mL) and trifluoroacetic acid (0.5 mL) is added. The mixture is stirred for 16 hrs and the solvent is removed in vacuo. The residue is dissolved in MeOH and filtered through StratoSphere PL-HCO3 MP SPE cartridge, concentrated and dried to give 50 mg of crude tetrahydro-pyran-4-carboxylic acid methyl-[5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-ylmethyl]-amide which is used without purification.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in MeOH
  3. filtrationfiltered through StratoSphere PL-HCO3 MP SPE cartridge
  4. concentrationconcentrated
  5. customdried

Sources & evidence

ORD record
ord-5cf7ab6395e546879b4444b1adf82dc1
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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