Trifluoroacetic acid → N-((6-(3-Chloro-4-fluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

HRID 2176496Notes

Reaction equation

HRID 2176496 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][NH:12][C:13]3[C:22]4[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][N:21]=4)[N:16]=[CH:15][CH:14]=3)=[N:9][N:10]=2)[CH:7]=1.BrC1C=CC2N(C(CNC(=O)OC(C)(C)C)=NN=2)C=1.[C:44](O)([C:46]([F:49])(F)F)=O.[Cl:51][C:52]1C=CN=[C:56]2[C:61]=1N=CC(OC)=[CH:57]2>C(Cl)Cl>[Cl:51][C:52]1[CH:61]=[C:56]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH2:11][NH:12][C:13]4[C:22]5[C:17](=[CH:18][C:19]([O:23][CH3:24])=[CH:20][N:21]=5)[N:16]=[CH:15][CH:14]=4)=[N:9][N:10]=3)[CH:7]=2)[CH:57]=[CH:44][C:46]=1[F:49]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 594273408-Chloro-3-methoxy-1,5-naphthyridineHCID 67502483N-((6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amineHCID 86630265Tert-butyl (6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methylcarbamate

Product 1

HCID 57691070N-((6-(3-Chloro-4-fluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-((6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-7-methoxy-1,5-naphthyridin-4-amine. To a suspension of tert-butyl (6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methylcarbamate (0.900 g, 2.75 mmol) in CH2Cl2 (10 mL) was added TFA (0.848 ml, 11.0 mmol) and the mixture stirred at rt. After 30 minutes additional TFA (0.848 ml, 11.0 mmol) was added, and the mixture stirred at rt 2 h more then concentrated. The residue was taken up into 2-butanol (5 mL) and combined with 8-chloro-3-methoxy-1,5-naphthyridine (0.535 g, 2.75 mmol) in a 5 mL microwave vessel. The vessel was sealed and the mixture heated in the microwave for 10 min at 120 C with a 60 sec prestir. The mixture was concentrated, diluted with DCM and stirred with 2N NaOH (pH 14) for 30 minutes. The solid was filtered to afford the title compound as a beige solid.

Workup

  1. stirringthe mixture stirred at rt 2 h more
  2. concentrationconcentrated
  3. customThe vessel was sealed
  4. temperaturethe mixture heated in the microwave for 10 min at 120 C with a 60 sec
  5. stirringprestir
  6. concentrationThe mixture was concentrated
  7. additiondiluted with DCM
  8. stirringstirred with 2N NaOH (pH 14) for 30 minutes
  9. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-78cf02418cfe4b9f9361dfbfe561ccac
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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