2-Methoxyethylamine → HCID 86591466, compound

HRID 387895Notes

Reaction equation

HRID 387895 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7]([NH:9][C:10]1[CH:29]=[CH:28][C:13]([O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]([OH:27])=[O:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=1)=[O:8].Cl.[CH2:31](N=C=NCCCN(C)C)C.[OH2:42].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:60][O:61][CH2:62][CH2:63]N>CN(C)C=O.O.C(OCC)(=O)C>[CH3:31][O:42][C:21]1[CH:20]=[C:19]2[C:24]([C:15]([O:14][C:13]3[CH:12]=[CH:11][C:10]([NH:9][C:7]([NH:6][C:2]4[S:1][CH:5]=[CH:4][N:3]=4)=[O:8])=[CH:29][CH:28]=3)=[CH:16][CH:17]=[N:18]2)=[CH:23][C:22]=1[C:25]([O:27][CH2:63][CH2:62][O:61][CH3:60])=[O:26]

Participants

9

Reactant 5

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86653608HCID 86653608, compound

Product 1

HCID 86591466HCID 86591466, compoundYield 24.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 7-methoxy-4-(4-(4-(((1,3-thiazol-2-ylamino)carbonyl)amino)phenoxy)-6-quinolinecarboxylic acid (87.3 mg, 0.20 mmol) in dimethylformamide (1 ml), there were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (58 mg, 0.30 mmol), 1-hydroxy-1H-benzotriazole monohydrate (41 mg, 0.30 mmol), triethylamine (0.084 ml, 0.60 mmol) and 2-methoxyethylamine (0.052 ml, 0.60 mmol) while stirring on ice, and the mixture was stirred at room temperature for 5 hours. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. After distilling off the solvent, ethyl acetate and then hexane was added to precipitate crystals, which were filtered out and dried under reduced pressure to obtain the title compound (24.4 mg, 0.049 mmol, 24.7%) as white crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent, ethyl acetate
  5. additionhexane was added
  6. customto precipitate crystals, which
  7. filtrationwere filtered out
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-839126db82dc494ca913e202ae97f9c9
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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