4-Methylmorpholine → HCID 178451528, compound

HRID 2173715Notes

Reaction equation

HRID 2173715 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]=[C:19]2[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][C:18]=12.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]=[C:19]3[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][C:18]=23)=[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 178451527HCID 178451527, compound

Product 1

HCID 178451528HCID 178451528, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 3-Amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (Intermediate 2)(0.102 g, 0.357 mmol), tert-butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate (0.08 g, 0.357 mmol), HATU (0.136 g, 0.357 mmol) and N-methylmorpholine (0.071 ml, 0.713 mmol) in DMF (5 ml) was stirred at RT for 30 minutes. The reaction mixture was diluted with water (15 ml) and the resulting orange precipitate was filtered under vacuum and washed with water (10 ml). 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 a yellow solid.

Workup

  1. filtrationthe resulting orange precipitate was filtered under vacuum
  2. washwashed with water (10 ml)
  3. customPurification of the resulting solid by chromatography on silica eluting with iso-hexane

Sources & evidence

ORD record
ord-458b9a33df4e433b89e2743c2ffcc2f4
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

Loading…