4-Methylmorpholine → HCID 178507662, compound

HRID 2173716Notes

Reaction equation

HRID 2173716 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([OH:15])=O)=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[NH:16]1[C:20]2=[N:21][CH:22]=[CH:23][N:24]=[C:19]2[C:18]([NH2:25])=[N:17]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([C:13]([NH:25][C:18]2[C:19]3=[N:24][CH:23]=[CH:22][N:21]=[C:20]3[NH:16][N:17]=2)=[O:15])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 584423503-Amino-6-bromo-5-(trifluoromethyl)picolinic acid2×HCID 178509233HCID 178509233, compound

Product 1

HCID 178507662HCID 178507662, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid (Intermediate 3) (0.10 g, 0.351 mmol), 1H-pyrazolo[3,4-b]pyrazin-3-amine (0.047 g, 0.702 mmol), HATU (0.133 g, 0.351 mmol) and N-methylmorpholine (0.069 ml, 0.702 mmol) in DMF (5 ml) was stirred at 75° C. for 90 minutes. After cooling to RT, the mixture was diluted with water (30 ml) and the resulting orange precipitate was filtered under vacuum and washed with water. Purification of the resulting solid by chromatography on silica eluting with iso-hexane:EtOAc (gradient of 0 to 100% EtOAc) to afforded the title compound as an orange solid.

Workup

  1. filtrationthe resulting orange precipitate was filtered under vacuum
  2. washwashed with water
  3. customPurification of the resulting solid by chromatography on silica eluting with iso-hexane

Sources & evidence

ORD record
ord-147449a9989949d3a472fa2aa7dbdb6e
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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