Hydrochloric Acid → HCID 66774827, compound

HRID 1594189Notes

Reaction equation

HRID 1594189 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.ClC1C=CC(CNC([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37](N(CCC(O)=O)CCC2C=C(OC)C=CC=2OC)=[O:38])=O)=CC=1.Cl.C(N=C=N[CH2:65][CH2:66][CH2:67][N:68]([CH3:70])C)C.O.ON1[C:77]2[CH:78]=[CH:79][CH:80]=[CH:81][C:76]=2N=N1.Cl.CN(C)[CH:85]=[O:86]>C(OCC)(=O)C>[CH3:85][O:86][C:37](=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:26]1[CH:25]=[CH:30][C:29]([CH2:70][N:68]([C:6]([C:5]2[CH:9]=[C:10]([O:14][CH3:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:8])[CH2:67][CH2:66][CH2:65][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)=[CH:28][CH:27]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 83573,4,5-Trimethoxybenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 9830171HCID 9830171, compound

Product 1

HCID 66774827HCID 66774827, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4,5-trimethoxybenzoic acid (368 mg) in N,N-dimethylformamide (10 ml) were added the compound prepared in reference example 8 (416 mg) and 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (461 mg) and 1-hydroxybenzotriazole hydrate (260 mg). The reaction mixture was stirred for 4 hours at room temperature. To the reaction mixture were added 1N hydrochloric acid and ethyl acetate and extracted. The extract was washed with a saturated aqueous solution of sodium bicarbonate and brine and dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give the compound (273 mg) having the following physical data.

Workup

  1. extractionextracted
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-3ef3f049ee35434a8c7a5fd66be35020
Source dataset
uspto-grants-2007_11
Patent number
US07300917B2

Reaction notes

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