Triethylamine → HCID 1506501, compound

HRID 493382Notes

Reaction equation

HRID 493382 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].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.[F:42][C:43]1[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=1>O1CCCC1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:47][C:46]2[CH:48]=[CH:49][C:43]([F:42])=[CH:44][CH:45]=2)=[O:10])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 114704-Acetylbenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 1506501HCID 1506501, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A mixture containing 4-acetyl-benzoic acid (4 g, 0.0243 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.13 g, 0.02673 mol), triethylamine (3.7 ml, 0.02673 mol), 1-hydroxybenzotriazole (3.62 g, 0.02673 mol) and 4-fluoroaniline (2.81 ml; 0.02916 mol) in 60 ml of tetrahydrofuran is stirred for 48 hours at 23° C. The reaction medium is filtered on frit and evaporated to dryness. The residue is taken up in a mixture of solvents : ethyl acetate-water: 50-50. The precipitate is filtered on frit, washed with isopropyl ether then isopentane. After drying, a white-coloured powder is obtained.

Workup

  1. filtrationThe reaction medium is filtered on frit
  2. customevaporated to dryness
  3. additionThe residue is taken up in a mixture of solvents
  4. filtrationThe precipitate is filtered on frit
  5. washwashed with isopropyl ether
  6. customAfter drying
  7. customa white-coloured powder is obtained

Sources & evidence

ORD record
ord-49350daa72a443c792bc282addb34484
Source dataset
uspto-grants-2009_05
Patent number
US07534805B2

Reaction notes

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