2-Chlorobenzoic Acid → HCID 69421311, compound

HRID 915546Notes

Reaction equation

HRID 915546 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][S:14]([NH2:17])(=[O:16])=[O:15])[CH2:8][CH2:7]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:43][C:44]1[CH:52]=[CH:51][CH:50]=[CH:49][C:45]=1[C:46](O)=[O:47]>CN(C1C=CN=CC=1)C.ClCCl>[Cl:43][C:44]1[CH:52]=[CH:51][CH:50]=[CH:49][C:45]=1[C:46]([NH:17][S:14]([CH2:13][CH2:12][N:9]1[CH2:10][CH2:11][CH:6]([O:5][C:4]2[CH:18]=[CH:19][C:20]([Cl:21])=[C:2]([Cl:1])[CH:3]=2)[CH2:7][CH2:8]1)(=[O:15])=[O:16])=[O:47]

Participants

7

Reactant 4

HCID 83742-Chlorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69418756HCID 69418756, compound

Product 1

HCID 69421311HCID 69421311, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(3,4-Dichlorophenoxy)-1-piperidineethanesulfonamide (0.1 g), EDCI (0.108 g), HOBT (40 mg), DMAP (40 mg) and 2-chlorobenzoic acid (88 mg) were dissolved in dichloromethane (5 mL) and triethyalamine (0.5 mL) was added. The reaction mixture was stirred for 17 h. The solvents were evaporated. The residue was purified by HPLC (gradient Ammonium acetate/Acetonitrile 95% to 25%; Xterra column) to give the subtitle compound (40 mg)

Workup

  1. additiontriethyalamine (0.5 mL) was added
  2. customThe solvents were evaporated
  3. customThe residue was purified by HPLC (gradient Ammonium acetate/Acetonitrile 95% to 25%; Xterra column)

Sources & evidence

ORD record
ord-da32845f59e549dd969b2effa2f9680b
Source dataset
uspto-grants-2007_09
Patent number
US07265227B2

Reaction notes

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