Benzoic Acid → HCID 58824182, compound

HRID 460054Notes

Reaction equation

HRID 460054 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[C:22]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:31]=[C:32]([S:36]([NH2:39])(=[O:38])=[O:37])[O:33][C:34]=2[CH3:35])=[CH:24][CH:23]=1>O1CCCC1.CN(C)C=O.CN(C1C=CN=CC=1)C>[C:1]([NH:39][S:36]([C:32]1[O:33][C:34]([CH3:35])=[C:30]([CH2:29][O:28][C:25]2[CH:26]=[CH:27][C:22]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:23][CH:24]=2)[CH:31]=1)(=[O:38])=[O:37])(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 243Benzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58824168HCID 58824168, compound

Product 1

HCID 58824182HCID 58824182, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of benzoic acid (61 mg) in a mixture of tetrahydrofuran (10 mL) and N,N-dimethylformamide (5 mL) was added 4-(N,N-dimethylamino)pyridine (3.0 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (118 mg) and 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-sulfonic acid amide (45) (206 mg). After 16 hours at room temperature the reaction mixture was concentrated in-vacuo, then partitioned between 0.1 M hydrochloric acid (30 mL) and ethyl acetate (3×30 mL). The combined organic extracts were washed with brine (25 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by HPLC to give compound 46 as light beige solid (17 mg). LC/MS System C: Rt=5.69 mins, m/z (ES−)=446 (M− for C25H21NO5S).

Workup

  1. concentrationAfter 16 hours at room temperature the reaction mixture was concentrated in-vacuo
  2. custompartitioned between 0.1 M hydrochloric acid (30 mL) and ethyl acetate (3×30 mL)
  3. washThe combined organic extracts were washed with brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-1ee31cff4ca84efd9bd9bdf64af6a1ab
Source dataset
uspto-grants-2007_03
Patent number
US07196089B2

Reaction notes

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