Methylamine → HCID 72948199, compound

HRID 1775454Notes

Reaction equation

HRID 1775454 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-53903977de544c4cb0db3fd0fc632a2c
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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