Ammonia → HCID 57690914, compound

HRID 219135Notes

Reaction equation

HRID 219135 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:17]([CH2:20][O:21][C:22]4[C:31]5[C:26](=[CH:27][C:28]([O:32][CH3:33])=[CH:29][CH:30]=5)[N:25]=[CH:24][CH:23]=4)=[N:18][N:19]=3)[CH:16]=2)[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C[N:35](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:17]([CH2:20][O:21][C:22]4[C:31]5[C:26](=[CH:27][C:28]([O:32][CH3:33])=[CH:29][CH:30]=5)[N:25]=[CH:24][CH:23]=4)=[N:18][N:19]=3)[CH:16]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:35])=[O:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57691292HCID 57691292, compound

Product 1

HCID 57690914HCID 57690914, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-fluoro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)benzoic acid (0.192 g, 0.43 mmol), HATU (0.26 g, 0.69 mmol), and Hunig'sBase (0.30 ml, 1.7 mmol) in DMF (10.75 mL) was allowed to stir for 30 minutes. Ammonia (0.0093 ml, 0.43 mmol) was then bubbled through the mixture for another 30 minutes. The solution was concentrated in vacuo and purified using via flash chromatography, eluting with 5-10% MeOH/NH4OH in DCM. There remained an unidentified peak in the NMR, so the solid was triturated in MeCN, filtered, and quickly washed with DCM to wash through the impurities. Concentration in vacuo yielded 2-fluoro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)benzamide as an off-white solid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified
  3. washeluting with 5-10% MeOH/NH4OH in DCM
  4. customso the solid was triturated in MeCN
  5. filtrationfiltered
  6. washquickly washed with DCM
  7. washto wash through the impurities
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-5914a5701fa24030850658a85b7f2897
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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