Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 71715067, compound

HRID 2206595Notes

Reaction equation

HRID 2206595 reaction equation
[CH3:1][O:2][CH:3]([CH3:19])[CH:4]([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15]([OH:17])=O)=[C:7]1[CH3:18])[CH3:5].Cl.[NH2:21][CH2:22][C:23]1[C:24](=[O:32])[NH:25][C:26]([CH3:31])=[CH:27][C:28]=1[O:29][CH3:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.[Cl-].[Na+].O>[CH3:30][O:29][C:28]1[CH:27]=[C:26]([CH3:31])[NH:25][C:24](=[O:32])[C:23]=1[CH2:22][NH:21][C:15]([C:8]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:6]([CH:4]([CH:3]([O:2][CH3:1])[CH3:19])[CH3:5])[C:7]=1[CH3:18])=[O:17]

Participants

6

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 89740341HCID 89740341, compoundHCID 1177786071-(3-methoxybutan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Product 1

HCID 71715067HCID 71715067, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
27 °C

Procedure

To a solution of 1-(3-methoxybutan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (2.4 g, 9.15 mmol) in DMF (30 mL) was added TEA (4.2 g, 41.50 mmol), 3-(aminomethyl)-4-methoxy-6-methylpyridin-2(1H)-one hydrochloride (2.1 g, 12.81 mmol) After stirred for 10 minutes at 27° C., the mixture was cooled and added HATU (5.56 g, 14.64 mmol). The mixture was stirred at 27° C. for 72 hours and 30% of S.M. remained. Then the mixture was heated at 80° C. for 5 hours. The solution was diluted with brine (100 mL) and extracted with CH2Cl2 (100 mL*3). The extractions were combined and dried over Na2SO4. The solvent was evaporated under vacuum and the residue was purified by flash column (Eluent: dichloromethane:methanol=95:5) to give N-((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-(3-methoxybutan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide. (3.6 g, yield 95%)

Workup

  1. temperaturethe mixture was cooled
  2. stirringThe mixture was stirred at 27° C. for 72 hours
  3. temperatureThen the mixture was heated at 80° C. for 5 hours
  4. extractionextracted with CH2Cl2 (100 mL*3)
  5. extractionThe extractions
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated under vacuum
  8. customthe residue was purified by flash column (Eluent: dichloromethane:methanol=95:5)

Sources & evidence

ORD record
ord-5c90d9c786124da2b35752a34862281a
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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