Methylamine → HCID 22929860, compound

HRID 1295930Notes

Reaction equation

HRID 1295930 reaction equation
[N:1]([CH2:4][C:5]1[C:13]([C:14]#[N:15])=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([O:16][CH2:17][CH3:18])[CH:6]=1)=[N+:2]=[N-:3].O1CCCC1.CN.[CH2:26]([N:28](CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH3:26][NH:28][C:9](=[O:11])[C:8]1[CH:12]=[C:13]([C:14]#[N:15])[C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:6][C:7]=1[O:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 22929650HCID 22929650, compound

Product 1

HCID 22929860HCID 22929860, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 4-(azidomethyl)-5-cyano-2-ethoxybenzoic acid in dimethylformamide (20 ml), a 2M tetrahydrofuran solution of methylamine (4.2 ml), diethyl phosphonocyanidate (1.28 ml) and triethylamine (1.27 ml) were added while cooling on ice. The mixture was stirred at room temperature overnight, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to yield the title compound (931 mg).

Workup

  1. temperaturewhile cooling on ice
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-86c5dfbc274547f0b41132e8c6300031
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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