Pyridine → HCID 71555127, compound

HRID 2407549Notes

Reaction equation

HRID 2407549 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[CH2:14][CH:13]2[CH:10]([CH2:11][NH:12]2)[CH2:9]1)=[O:7].C(N(CC)CC)C.N1C=CC=CC=1.[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[CH2:4][NH:5][C:6]([N:8]1[CH2:14][CH:13]2[CH:10]([CH2:11][N:12]2[S:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:41])=[O:40])[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 89523946HCID 89523946, compound

Product 1

HCID 71555127HCID 71555127, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-3,6-diaza-bicyclo[3.2.0]heptane-3-carboxylic acid 2,4-dichloro-benzylamide (150 mg, 270 μmol) in dichloromethane (6 mL) were added triethylamine (82 mg, 810 μmol), pyridine (1 mL) and benzenesulfonyl chloride (52 mg, 297 μmol). The reaction mixture was stirred at ambient temperature overnight before concentrating in vacuo. Purification by chromatography (SiO2; dichloromethane:methanol 1:0 to 19:1) afforded the title compound (56 mg, 47%) as a colorless solid. MS (EI) m/e: 440.1 (M+H)+.

Workup

  1. concentrationbefore concentrating in vacuo
  2. customPurification by chromatography (SiO2; dichloromethane:methanol 1:0 to 19:1)

Sources & evidence

ORD record
ord-5b41a25e801a4ed6b22b7f365c166c6e
Source dataset
uspto-grants-2014_08
Patent number
US08809552B2

Reaction notes

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