Methylamine hydrochloride → HCID 86687950, compound

HRID 2406331Notes

Reaction equation

HRID 2406331 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([OH:14])=O)=[CH:4][CH:3]=1.Cl.CN.[CH3:18][N:19](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([NH:19][CH3:18])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 211934708-Amino-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Product 1

HCID 86687950HCID 86687950, compoundYield 117.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 50-mL round bottom flash was charged with 8-amino-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid (200 mg, 1.025 mmol), methylamine hydrochloride (138 mg, 2.05 mmol), HATU (467 mg, 1.23 mmol), TEA (0.5 mL), and DMF (5.0 mL). The reaction mixture was stirred at room temperature for 15 h. It was then purified by reverse-phase Combi-Flash eluting with 0.1% NH4HCO3 in water/CH3CN to afford the title compound as red oil (250 mg, 88%). LCMS: ESI (3 minute run), m/z=209.1 [M+1]+; Retention time: 1.53 minute.

Workup

  1. customIt was then purified by reverse-phase Combi-Flash
  2. washeluting with 0.1% NH4HCO3 in water/CH3CN

Sources & evidence

ORD record
ord-9f4d3ce436814c5aa8b25e13019a9d95
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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