Benzoic Acid → HCID 24804586, compound

HRID 2197446Notes

Reaction equation

HRID 2197446 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.Cl.[S:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]1[N:38]=[C:37]([CH:39]2[CH2:44][CH2:43][NH2+:42][CH2:41][CH2:40]2)[O:36][N:35]=1>ClCCl>[C:2]1([C:1]([N:42]2[CH2:43][CH2:44][CH:39]([C:37]3[O:36][N:35]=[C:34]([C:30]4[S:29][CH:33]=[CH:32][CH:31]=4)[N:38]=3)[CH2:40][CH2:41]2)=[O:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 8471Triethylamine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 86654171HCID 86654171, compound

Product 1

HCID 24804586HCID 24804586, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

67.40 mg (1 eq.) of benzoic acid, 106 mg (1 eq.) of EDCI and 165 μl (2 eq.) of triethylamine were dissolved in 2 ml of dichloromethane. 150 mg (1 eq.) of 4-(3-thiophen-2-yl[1,2,4]oxadiazol-5-yl)piperidinium hydrochloride dissolved in 2 ml of dichloromethane and 165 μl (2 eq.) of triethylamine were added to the reaction medium, which was stirred at room temperature overnight. The reaction medium was evaporated under reduced pressure and the residue was chromatographed on a thick layer (eluent: CH2Cl2/MeOH (98/2: v/v)) to give 98 mg (52%) of the expected product.

Workup

  1. customThe reaction medium was evaporated under reduced pressure
  2. customthe residue was chromatographed on a thick layer (eluent: CH2Cl2/MeOH (98/2: v/v))

Sources & evidence

ORD record
ord-1fa25c6e486141439f9a8cd75a06f692
Source dataset
uspto-grants-2012_12
Patent number
US08338599B2

Reaction notes

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