Methylamine → HCID 22103818, compound

HRID 1912765Notes

Reaction equation

HRID 1912765 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CN.O.[N:16]1(O)[C:20]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:20][NH:16][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)=[O:12]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 742801H-Indole-5-Carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 22103818HCID 22103818, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5 mL of N,N-dimethylformamide, 500 mg (3.1 mmol) of 1H-indole-5-carboxylic acid, 750 mg (9.3 mmol) of 40% methylamine, 477 mg (3.1 mmol) of benzotriazole-1-ol hydrate and 713 mg (3.8 mmol) of (3-dimethylaminopropyl)ethylcarbodiimide hydrochloride were dissolved and the solution was stirred at room temperature for three hours, and then the solvent was distilled under reduced pressure. The obtained residue was dissolved in ethyl acetate and washed with a saturated sodium hydrogencarbonate solution (50 mL, twice) and a saturated saline (50 mL) in the order named. The organic layer was dried and then concentrated to obtain 397 mg (73%) of a crude product of 1H-indole-5-carboxylic acid methylamide. The product was used in the next reaction without further purification.

Workup

  1. distillationthe solvent was distilled under reduced pressure
  2. dissolutionThe obtained residue was dissolved in ethyl acetate
  3. washwashed with a saturated sodium hydrogencarbonate solution (50 mL
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-41bbcb1f6c254e8b8e240920527996fb
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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