2-Naphthalenesulfonyl chloride → HCID 11338751, compound

HRID 1984541Notes

Reaction equation

HRID 1984541 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]2=[O:23])[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[S:34](Cl)(=[O:36])=[O:35].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[S:34]([N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:15]1=[O:23])(=[O:35])=[O:36]

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 13046891tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 11338751HCID 11338751, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-(2-oxo-2,3-dihydrobenzimidazol-1-yl)piperidine-1-carboxylic acid t-butyl ester (64 mg, 0.2 mmol) in CH2Cl2 at room temperature is treated with 2-naphthylsulfonyl chloride (50 mg, 0.2 mmol) followed by diisopropylethylamine (174 uL, 1.0 mmol) and 4-dimethylaminopyridine (24 mg, 0.2 mmol), stirred at 60° C. for 16 h and concentrated in vacuo. The resultant residue is dissolved in THF, treated with HCl in dioxane (4 N) (1 mL), stirred for 4 h and concentrated in vacuo. This residue is dissolved in a mixture of DMSO, methanol and water and purified by Gilson1 preparative HPLC to give the title product, 24 mg, [M+H] 408, retention time (RT) 1.89 minutes. 1Gilson Preparative HPLC conditions: Gilson Preparative HPLC system; YMC Pro C18, 20 mm×50 mm ID, 5 uM column; 2 mL injection; Solvent A: 0.02% TFA/water; Solvent B: 0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 2 min: 95% A; 14 min: 10% A, 15 min: 10% A, 16 min: 95% A; Flow rate 22.5 mL/min; Detection: 254 nm DAD.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in THF
  3. additiontreated with HCl in dioxane (4 N) (1 mL)
  4. stirringstirred for 4 h
  5. concentrationconcentrated in vacuo
  6. dissolutionThis residue is dissolved in a mixture of DMSO, methanol and water
  7. custompurified by Gilson1 preparative HPLC

Sources & evidence

ORD record
ord-6fe6a3e743604a5f8224f9d5f96ae2f9
Source dataset
uspto-grants-2009_06
Patent number
US07544701B2

Reaction notes

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