4-Chlorobenzoic Acid → HCID 86631279, compound

HRID 1260916Notes

Reaction equation

HRID 1260916 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](O)=[O:38])=[CH:35][CH:34]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(#N)C.O.C(N(CC)CC)C>[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:12][C@@H:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:38])=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86631280HCID 86631280, compound

Product 1

HCID 86631279HCID 86631279, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of the compound (0.50 g) obtained in step 4, 4-chlorobenzoic acid (0.35 g) and triethylamine (0.16 mL) in acetonitrile (15 mL) were added WSC.HCl (0.43 g) and HOBt (0.34 g), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; 33% ethyl acetate/hexane) to give the title compound (0.42 g, 91%) as a white powder.

Workup

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent; 33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4b06fbf16d7a4a3a8c795da101d4dc33
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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