Triethylamine → HCID 12094482, compound

HRID 1168625Notes

Reaction equation

HRID 1168625 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:13][C:14]([CH3:19])([CH3:18])[CH2:15][CH2:16][NH2:17].[CH2:20](N(CC)CC)[CH3:21].Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:17][CH2:16][CH:15]2[CH2:21][CH2:20][CH2:13][C:14]2([CH3:19])[CH3:18])=[O:10])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 114704-Acetylbenzoic AcidHCID 197093,3-DimethylbutylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 12094482HCID 12094482, compoundYield 65.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Acetylbenzoic acid (200 mg, 1.20 mmol) and amine 2 (from Example 1, 199 mg, 1.22 mmol) were dissolved in 5 mL of dichloromethane and triethylamine (187 μL, 1.34 mmol) and 4-dimethylaminopyridine (15 mg, 0.12 mmol) were added. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (398 mg, 1.34 mmol) was added and the mixture was stirred for 18 hours. The reaction was diluted with ethyl acetate and washed with hydrochloric acid (1.0 M, aq.), sodium bicarbonate (sat'd., aq.) and sodium chloride (sat'd., aq.). The organic layer was dried over magnesium sulfate, filtered and the solvent removed to yield 216 mg (65%) of a white solid.

Workup

  1. washwashed with hydrochloric acid (1.0 M, aq.), sodium bicarbonate (sat'd., aq.) and sodium chloride (sat'd., aq.)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed

Sources & evidence

ORD record
ord-808bc8a646a64a22b7cf3a932bd7b712
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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