4-Methylmorpholine → HCID 178508424, compound

HRID 2173718Notes

Reaction equation

HRID 2173718 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])[N:7]=1.[NH2:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[NH:19][N:18]=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:16][C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:19][N:18]=2)=[O:15])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:9])([F:10])[F:11])[N: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 58442296HCID 58442296, compound2×HCID 178509226HCID 178509226, compound

Product 1

HCID 178508424HCID 178508424, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture comprising 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (Intermediate 2) (0.320 g, 1.118 mmol), 3-aminopyrazolo[3,4-b]pyridine (0.150 g, 1.118 mmol) and HATU (0.425 g, 1.118 mmol) in DMF (5 ml) was treated with N-methylmorpholine (0.111 ml, 1.118 mmol) and stirred at 80° C. overnight. After cooling to RT, the mixture was diluted with water (25 ml) and the resulting yellow precipitate was filtered under vacuum and washed with water. The crude material was purified by chromatography on silica eluting with iso-hexane:EtOAc (gradient of 0 to 100 EtOAc) to give the title compound as a yellow solid.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe resulting yellow precipitate was filtered under vacuum
  3. washwashed with water
  4. customThe crude material was purified by chromatography on silica eluting with iso-hexane

Sources & evidence

ORD record
ord-aee5272df73e4ab980de3208a4dc50db
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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