Pyridine → HCID 58961389, compound

HRID 1776216Notes

Reaction equation

HRID 1776216 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.N1C=CC=CC=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH:1]1([NH:5][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 75645CyclobutylamineHCID 81531Diisopropylethylamine

Product 1

HCID 58961389HCID 58961389, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of cyclobutylamine (0.400 g, 5.6 mmol), N,N-diisopropylethylamine (0.930 mL, 5.6 mmol) and pyridine (0.455 mL, 5.6 mmol) in methylene chloride (10 mL) at 0° C. was slowly added methanesulfonyl chloride (0.435 mL, 5.6 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 16 hrs. The mixture was concentrated and the residue purified by silica gel chromatography (0-80% ethyl acetate/hexane) to afford the product as a low melting solid (0.82 g, 98%). 1H NMR (300 MHz, CDCl3) δ 4.62 (br s, 1H), 3.94 (m, 1H), 2.94 (s, 3H), 2.50-2.30 (m, 2H), 2.10-1.85 (m, 2H), 1.85-1.60 (m, 2H).

Workup

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. customthe residue purified by silica gel chromatography (0-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-41dcd95341cb49c9952f78d12b584ffc
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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