Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-Bromo-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246745Notes

Reaction equation

HRID 246745 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]([OH:13])=O)=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1.[CH3:14][C:15]1([NH2:18])C[CH2:16]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]([NH:18][CH:15]([CH3:16])[CH3:14])=[O:13])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 116511491-MethylcyclopropanamineHCID 866778972-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Product 1

HCID 866780102-Bromo-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 42.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-bromo-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (250 mg, 1.03 mmol), 1-methylcyclopropanamine (150 mg, 2.2 mmol) and HATU (456 mg, 1.2 mmol) in 20 mL of dry THF was stirred for 4 hours. The reaction mixture was evaporated to dryness, the residue suspended in 20 mL of 0.5 N HCl, product extracted with ethyl acetate (3×50 mL), organics combined dried with sodium sulfate, filtered and concentrated. The residue was triturated with petroleum ether (2 mL) then decanted and dried to give 2-bromo-N-isopropyl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (125 mg, crude). LCMS: (M+H)+=285/287.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionproduct extracted with ethyl acetate (3×50 mL)
  3. dry with materialorganics combined dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with petroleum ether (2 mL)
  7. customthen decanted
  8. customdried

Sources & evidence

ORD record
ord-a343c8ed0f1645549fc1b9aee109e545
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…