4-Methylmorpholine → HCID 71533330, compound

HRID 2173717Notes

Reaction equation

HRID 2173717 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[NH:21][N:20]=[CH:19][C:18]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=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[NH:21][N:20]=[CH:19][C:18]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=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 14777624-(2-Pyridinyl)-1H-pyrazol-3-amineHCID 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×

Product 1

HCID 71533330HCID 71533330, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (Intermediate 2) (0.179 g, 0.624 mmol), 5-amino-4-(pyridin-2-yl)-1H-pyrazole (0.1 g, 0.624 mmol), HATU (0.237 g, 0.624 mmol) and N-methylmorpholine (0.123 ml, 1.249 mmol) in DMF (5 ml) was stirred at 80° C. for 2.5 hours. After cooling to RT, the mixture was diluted with water (40 ml) and the resulting yellow precipitate was filtered under vacuum and washed with water (20 ml). MeOH (150 ml) was added to the solid and the suspension ultrasonicated to give a fine suspension. The suspension was filtered under vacuum and the solid was rinsed with MeOH (20 ml) and dried under vacuum at 45° C. for 1.5 hours to afford the title compound as a yellow solid.

Workup

  1. filtrationthe resulting yellow precipitate was filtered under vacuum
  2. washwashed with water (20 ml)
  3. additionMeOH (150 ml) was added to the solid
  4. customthe suspension ultrasonicated
  5. customto give a fine suspension
  6. filtrationThe suspension was filtered under vacuum
  7. washthe solid was rinsed with MeOH (20 ml)
  8. customdried under vacuum at 45° C. for 1.5 hours

Sources & evidence

ORD record
ord-e5e86b7a72c84dabb34c2e4825ddab7e
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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