Methylamine → HCID 178485555, compound

HRID 1488231Notes

Reaction equation

HRID 1488231 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.C[CH2:11][N:12]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CN>CN(C=O)C>[CH3:11][NH:12][C:7]([C:5]1[N:6]=[C:2]([CH3:1])[NH:3][CH:4]=1)=[O:9]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178433052HCID 178433052, compound

Product 1

HCID 178485555HCID 178485555, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyl-1H-imidazole-4-carboxylic acid (378 mg, 3 mmol), EDCI (745 mg, 3.9 mmol), HOBt (253 mg, 1.5 mmol), DIEA (1.6 mL, 9 mmol) and methyl amine (2M in THF) (3.6 mL, 7.2 mmol) were dissolved in DMF (10 mL) and stirred at room temperature for 16 hours. After removal of DMF, the residue was dry loaded and purified by flash chromatography (SiO2, 0-10% methanol in DCM and 1% NH4OH) to give 280 mg (67%) of the title compound. m/z (ES+) 140 (M+H)+.

Workup

  1. customAfter removal of DMF
  2. customthe residue was dry loaded
  3. custompurified by flash chromatography (SiO2, 0-10% methanol in DCM and 1% NH4OH)

Sources & evidence

ORD record
ord-f8554a003adc435d8021997c9e22fb4a
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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