Trifluoroacetic acid → HCID 117667718, compound

HRID 712744Notes

Reaction equation

HRID 712744 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:22]3[CH:23]=[N:24][C:25]4[N:26]([C:32](=[O:34])[NH2:33])[CH2:27][CH2:28][CH2:29][C:30]=4[CH:31]=3)[C:19]=2[C:20]#[N:21])[CH2:10][CH2:9]1)=O)(C)(C)C.F[C:36](F)(F)C(O)=O>C(Cl)Cl>[C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:22]3[CH:31]=[C:30]4[C:25](=[N:24][CH:23]=3)[N:26]([C:32]([NH2:33])=[O:34])[CH2:27][CH2:28][CH2:29]4)[C:19]=2[C:20]#[N:21])[CH2:12][CH2:13]1)(=[O:5])[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117667610HCID 117667610, compound

Product 1

HCID 117667718HCID 117667718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 5-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-4-cyano-3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.22 mmol) is dissolved in DCM (2.0 mL) and trifluoroacetic acid (0.5 mL) is added. The mixture is stirred for 16 hrs and all the solvent is removed in vacuo. The residue is dissolved in MeOH and is passed through StratoSpheres SPE PL-HCO3 cartridge. The solution is concentrated to give the crude 6-(4-cyano-1′,2′,3′,4′,5′,6′-hexahydro-[3,4]bipyridinyl-5-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide which is used without purification.

Workup

  1. customall the solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in MeOH
  3. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-21b0329aaac94acaa2e47404b5c2c3e1
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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