Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 58565345, compound

HRID 2175350Notes

Reaction equation

HRID 2175350 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[C:19]([OH:21])=O)#[N:2].F[P-](F)(F)(F)(F)F.[N:29]1([O:38][C:39](N(C)C)=[N+](C)C)[C:33]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CNOC>CN(C)C=O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[C:19]([N:29]([O:38][CH3:39])[CH3:33])=[O:21])#[N:2]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58565339HCID 58565339, compound

Product 1

HCID 58565345HCID 58565345, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-cyano-1-(3-fluorophenyl)-1H-indole-2-carboxylic acid (0.12 g, 0.43 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.32 g, 0.86 mmol) and N,N-diisopropylethylamine (0.37 mL, 2.1 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 10 minutes. N,O-Dimethylhydroxylamine hydrochloride (63 mg, 0.64 mmol) was added and the resulting suspension was stirred at room temperature overnight. The mixture was quenched with water and extracted with EtOAc. The extracts were combined, dried over MgSO4, concentrated, and purified on silica gel (eluting with 0-25% EtOAc/hexane) to give the desired product (90 mg, 65%). LCMS calculated for C18H15FN3O2(M+H)+: m/z=324.1. Found: 324.0.

Workup

  1. stirringthe resulting suspension was stirred at room temperature overnight
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel (eluting with 0-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-5a6116f9971c4a2dbac3ec0eb44757fe
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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