Methylamine → HCID 72948199, compound

HRID 2207750Notes

Reaction equation

HRID 2207750 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[C:16]([NH:18][CH3:19])=[O:17].O1CCCC1.[C:25](N1C=CN=C1)([N:27]1C=CN=[CH:28]1)=[O:26].CN>C(N(CC)CC)C>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:16]([NH:18][CH3:19])=[O:17])=[C:5]2[CH2:4][CH2:3][NH:2][C:25](=[O:26])[NH:27][CH3:28]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 118071469HCID 118071469, compound

Product 1

HCID 72948199HCID 72948199, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 3-(2-aminoethyl)-5-methoxy-N-methyl-1H-indole-2-carboxamide hydrochloride (167 mg) were added tetrahydrofuran (2.00 mL), triethylamine (0.246 mL), and 1,1′-carbonyldiimidazole (143 mg), followed by stirring at room temperature for 15 minutes. Then, methylamine (2 M tetrahydrofuran solution, 1.77 mL) was added thereto, followed by warming to 50° C. and stirring for 1 hour. The reaction mixture was cooled to room temperature, silica gel was added thereto, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 20:1) to obtain 5-methoxy-N-methyl-3-{2-[(methylcarbamoyl)amino]ethyl}-1H-indole-2-carboxamide (144 mg) as a white solid.

Workup

  1. temperatureby warming to 50° C.
  2. stirringstirring for 1 hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionsilica gel was added
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 20:1)

Sources & evidence

ORD record
ord-0157ea57192945cb85301d15e3a09cc1
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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