Pyridine → HCID 71555127, compound

HRID 2281686Notes

Reaction equation

HRID 2281686 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-25b49da632994f55bb9c865c200e9f99
Source dataset
uspto-grants-2015_09
Patent number
US09139593B2

Reaction notes

Loading…