Methylamine → HCID 67264031, compound

HRID 1487223Notes

Reaction equation

HRID 1487223 reaction equation
CN.[NH2:3][C:4]1[C:12]2[O:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][C:5]=1[C:13]([OH:15])=O.C[CH2:17][N:18](C(C)C)C(C)C>C(#N)C>[NH2:3][C:4]1[C:12]2[O:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][C:5]=1[C:13]([NH:18][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 19064849HCID 19064849, compound

Product 1

HCID 67264031HCID 67264031, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methylamine (0.43 g, 13.9 mmol, prepared from 33% aqueous solution and sodium hydroxide) in acetonitrile (20 mL) was added 4-aminobenzo[d][1,3]dioxole-5-carboxylic acid (1.68 g, 9.3 mmol), N,N′-diisopropylethylamine (3.24 mL, 18.6 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N″-tetramethyluronium hexafluorophosphate (HATU, 4.28 g, 11.2 mmol). The mixture was stirred at room temperature for 12 hours, and then evaporated. The residue was diluted with dichloromethane, washed by water, dried over anhydrous sodium sulfate, concentrated and purified by silica gel chromatography to afford the product 4-amino-N-methylbenzo[d][1,3]dioxole-5-carboxamide (1.48 g, yield 82%). 1H NMR (400 MHz, CDCl3) δ ppm 6.95-6.98 (d, 1H, J=8.4 Hz), 6.24-6.26 (d, 1H, J=8.0 Hz), 5.97 (s, 2H), 2.94-2.95 (m, 3H).

Workup

  1. customevaporated
  2. additionThe residue was diluted with dichloromethane
  3. washwashed by water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-60840d762ea44f839200bd9cbc140e12
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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