4-Methylmorpholine → HCID 178508421, compound

HRID 2173713Notes

Reaction equation

HRID 2173713 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.[N:16]1([CH2:22][C:23]2[CH:27]=[C:26]([NH2:28])[NH:25][N:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]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>[N:16]1([CH2:22][C:23]2[CH:27]=[C:26]([NH:28][C:13]([C:3]3[C:2]([NH2:1])=[N:7][C:6]([C:8]([F:9])([F:10])[F:11])=[C:5]([Br:12])[N:4]=3)=[O:15])[NH:25][N:24]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]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 178507695HCID 178507695, compound2×

Product 1

HCID 178508421HCID 178508421, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture, comprising 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (Intermediate 2)(0.349 g, 1.221 mmol), 3-(piperidin-1-ylmethyl)-1H-pyrazol-5-amine (Intermediate 8) (0.220 g, 1.221 mmol), HATU (0.464 g, 1.221 mmol) and N-methylmorpholine (0.241 ml, 2.441 mmol) in DMF (5 ml) was stirred for 30 minutes at RT. The reaction mixture was diluted with water (20 ml) and the resulting yellow precipitate was filtered under vacuum and washed with water (20 ml). The resulting residue was loaded onto a SCX-2 cartridge eluting with MeOH followed by 7M NH3 in MeOH. The methanolic ammonia fractions were concentrated in vacuo and the residue was triturated with EtOAc/iso-hexane to yield the title compound.

Workup

  1. filtrationthe resulting yellow precipitate was filtered under vacuum
  2. washwashed with water (20 ml)
  3. washeluting with MeOH
  4. concentrationThe methanolic ammonia fractions were concentrated in vacuo
  5. customthe residue was triturated with EtOAc/iso-hexane

Sources & evidence

ORD record
ord-1ccc1d91666f48ed8158f52af3d6f8de
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

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