Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 118344726, compound

HRID 1753071Notes

Reaction equation

HRID 1753071 reaction equation
[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:10]([O:18][CH3:19])=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN([C:39]([O:43][N:44]1N=NC2C=CC=N[C:45]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CONC>CN(C=O)C>[CH3:19][O:18][C:10]1[C:9]([N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:17][C:13]([C:14](=[O:16])[N:44]([O:43][CH3:39])[CH3:45])=[CH:12][N:11]=1

Participants

6

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 22271444HCID 22271444, compound

Product 1

HCID 118344726HCID 118344726, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[bis(tert-butoxycarbonyl)amino]-6-methoxynicotinic acid (Preparation 70, 500 mg, 1.358 mmol) and DIPEA (730 uL, 4.076 mmol) in DMF (4 mL) was added HATU (774 mg, 2.038 mmol) and N-methoxy-methylamine hydrochloride (198 mg, 2.038 mmol) and the reaction stirred at room temperature for 16 hours. The reaction was partitioned between saturated aqueous NaHCO3 solution and EtOAc, the organic layer collected, dried over sodium sulfate and concentrated in vacuo to afford the title compound that was used directly in the next step.

Workup

  1. customThe reaction was partitioned between saturated aqueous NaHCO3 solution and EtOAc
  2. customthe organic layer collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5aca984bcbbd4baea4b8a75c416b70bf
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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