Trifluoroacetic acid → HCID 22346392, compound

HRID 897325Notes

Reaction equation

HRID 897325 reaction equation
Br[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[NH:24]1[CH2:29][CH2:28][S:27][CH2:26][CH2:25]1.C(N(C(C)C)CC)(C)C.C(O)(C(F)(F)F)=O>CN1C(=O)N(C)CCC1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][NH:14][C:12]([C:10]2[C:9]([OH:23])=[C:8]3[C:3]([CH:4]=[CH:5][CH:6]=[N:7]3)=[C:2]([N:24]3[CH2:29][CH2:28][S:27][CH2:26][CH2:25]3)[N:11]=2)=[O:13])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 67164ThiomorpholineHCID 81531DiisopropylethylamineHCID 223464015-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 1

HCID 22346392HCID 22346392, compound

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

A solution of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (0.25 g, 0.67 mmol), thiomorpholine (0.19 mL, 2.0 mmol) and diisopropylethylamine (0.06 mL, 0.67 mmol) in DMPU (3.0 mL) were heated at 135 C for 23 hr. The reaction was cooled to room temperature, neutralized by the addition of TFA and purified by reverse phase HPLC. (Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins). Lyophilization of the pure fractions afforded the title compound as an off white solid.

Workup

  1. custompurified by reverse phase HPLC
  2. wash(Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins)

Sources & evidence

ORD record
ord-f9dc9ca208a243ca90bdc110c12c0fcb
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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