Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 58515992, compound

HRID 717856Notes

Reaction equation

HRID 717856 reaction equation
F[P-](F)(F)(F)(F)F.C[N+](C)=[C:10](N(C)C)[O:11][N:12]1[C:16]2N=CC=CC=2N=N1.[Cl:25][C:26]1[C:27]2[N:28]([N:42]=[CH:43][CH:44]=2)[C:29]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)=[C:30]([C:32](O)=[O:33])[CH:31]=1.C(N(CC)C(C)C)(C)C.Cl.CNOC>CN(C)C=O.C(OCC)(=O)C>[Cl:25][C:26]1[C:27]2[N:28]([N:42]=[CH:43][CH:44]=2)[C:29]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)=[C:30]([C:32]([N:12]([O:11][CH3:10])[CH3:16])=[O:33])[CH:31]=1

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58515926HCID 58515926, compound

Product 1

HCID 58515992HCID 58515992, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.46 g, 1.2 mmol) was added to a solution of 4-chloro-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carboxylic acid (0.29 g, 1.0 mmol) in N,N-dimethylformamide (3.0 mL) containing N,N-diisopropylethylamine (0.35 mL, 2.0 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.14 g, 1.5 mmol) at room temperature. The reaction was complete after stirring for 2 hours. This was taken up in ethyl acetate, washed with water, brine, dried over magnesium sulfate and concentrated to give the crude amide. The product was purified on silica gel eluting hexane:ethyl acetate gradient to give 4-chloro-7-(3-fluorophenyl)-N-methoxy-N-methylpyrazolo[1,5-a]pyridine-6-carboxamide (0.29 g, 88%) as a glass. LCMS calculated for C16H14ClFN3O2 (M+H)+: m/z=334.1. found: 333.9.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give the crude amide
  5. customThe product was purified on silica gel
  6. washeluting hexane

Sources & evidence

ORD record
ord-7784cdbcb7c04c3abe443792f5305fdd
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

Loading…