Potassium Carbonate → 5-Dibenzylamino-6-fluoro-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 732580Notes

Reaction equation

HRID 732580 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:13][N:14](C)[CH2:15][CH2:16][CH2:17]N=C=NCC.[CH2:24]([O:26][C:27](=[O:53])[C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([N:38]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:36]=1[F:37])[C:31](O)=[O:32])[CH3:25].CNCCC.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:24]([O:26][C:27](=[O:53])[C:28]1[C:36]([F:37])=[C:35]([N:38]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH:34]=[C:30]([C:31]([N:14]([CH3:13])[CH2:15][CH2:16][CH3:17])=[O:32])[CH:29]=1)[CH3:25]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 12315N-MethylpropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 688146125-Dibenzylamino-4-fluoro-isophthalic acid 3-ethyl ester

Product 1

HCID 688144355-Dibenzylamino-6-fluoro-N-methyl-N-propyl-isophthalamic acid ethyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve the 1-hydroxybenzotriazole hydrate (139 mg, 1.03 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (197 mg, 1.03 mmol) and 5-dibenzylamino-4-fluoro-isophthalic acid 3-ethyl ester (381 mg, 0.934 mmol) in dichloromethane (10.0 mL). Stir for 30 min. Add methylpropyl amine (68.3 mg, 0.93 mmol) to the reaction mixture. Stir the reaction for 4 h. Add 10% aqueous potassium carbonate solution (10 mL). Extract with dichloromethane (2×50 mL). Combine the organic layers, wash with water (20 mL), saturated aqueous sodium chloride (20 mL), dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 40:60 ethyl acetate:hexanes) to give the title compound (279 mg, 65%).

Workup

  1. stirringStir
  2. customthe reaction for 4 h
  3. extractionExtract with dichloromethane (2×50 mL)
  4. washCombine the organic layers, wash with water (20 mL), saturated aqueous sodium chloride (20 mL)
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 40:60 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-eaee806a0c2041d7b74918d01ce8daf2
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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