Methylamine → HCID 57721370, compound

HRID 1986102Notes

Reaction equation

HRID 1986102 reaction equation
CN.[CH2:3]([N:5](CC)CC)C.[Cl:10][C:11]1[N:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:12]=1[C:13](Cl)=[O:14]>CC#N>[Cl:10][C:11]1[N:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:12]=1[C:13]([NH:5][CH3:3])=[O:14]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 27999962,5-Dichloro-nicotinoyl chloride

Product 1

HCID 57721370HCID 57721370, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methanamine (0.355 mL, 2.85 mmol) and triethylamine (0.662 mL, 4.75 mmol) were dissolved in CH3CN (14.2 mL) at 23° C. 2,5-Dichloronicotinoyl chloride (500 mg, 2.376 mmol) was added and the reaction was stirred for 16 h. The solvent was removed by rotary evaporation and the residue was partitioned between EtOAc (20 mL) and 5% aq. NaHCO3 soln. (20 mL). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organics were washed with brine, dried over MgSO4 and concentrated. The resulting solid was triturated in 5% EtOAc-Hexane to provide the desired product as a cream powder (456.7 mg, 94%). 1H NMR (CD3OD) δ 8.46 (d, 1H, J=2.54 Hz), 7.96 (d, 1H, J=2.54 Hz), 2.90 (s, 3H); MS(ESI+) m/z 205.1 (M+H)+.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue was partitioned between EtOAc (20 mL) and 5% aq. NaHCO3 soln
  3. extractionThe aqueous phase was extracted with EtOAc (3×20 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting solid was triturated in 5% EtOAc-Hexane

Sources & evidence

ORD record
ord-8bd74a1360644b90b7ad1f45056afc28
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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