Pyridine → HCID 58046704, compound

HRID 2363067Notes

Reaction equation

HRID 2363067 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:37]=[CH:36][C:10]([CH2:11][N:12]2[C:16](=[O:17])[C:15]3([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[N:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:13]2)=[CH:9][CH:8]=1.N1C=CC=CC=1>ClCCl>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][N:12]2[C:16](=[O:17])[C:15]3([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[N:14]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:13]2)=[CH:36][CH:37]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 58046774HCID 58046774, compound

Product 1

HCID 58046704HCID 58046704, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.39 mL, 5.02 mmol) was added dropwise at 0° C. to tert-butyl 3-(4-aminobenzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (2.19 g, 5.02 mmol) and pyridine (0.61 mL, 7.53 mmol) in dichloromethane (10 mL). The reaction was allowed to warm to room temperature and stirred for 30 minutes. The mixture was diluted with dichloromethane, washed with 2M aqueous hydrochloric acid and brine, dried (MgSO4) and evaporated. The residue was purified by PTLC (50% ethyl acetate/hexanes) to give product as an oil (2.38 g, 92%); 1H NMR (DMSO-d6); δ1.45 (s, 9H); 1.63 (d, J=14 Hz, 2H); 2.18-2.23 (m, 2H); 2.98 (s, 3H); 3.30-3.55 (m, 2H); 3.80-3.95 (m, 2H); 4.52 (s, 2H); 4.59 (s, 2H); 6.67 (d, J=8 Hz, 2H); 6.76 (t, J=7.2 Hz, 2H); 7.15-7.21 (m, 4H); 7.26-7.28 (m, 2H); MS for C26H34N4O5S m/z 515 (M+H)+.

Workup

  1. washwashed with 2M aqueous hydrochloric acid and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by PTLC (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-24ba1cf1d87f45eb8aea6f31507b5911
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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