Methyl vinyl sulfone → HCID 59837356, compound

HRID 273055Notes

Reaction equation

HRID 273055 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:12][CH:11]=2)[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH3:26][S:27]([CH:30]=[CH2:31])(=[O:29])=[O:28]>CO>[CH3:1][N:2]([CH2:3][C:4]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[CH:14][CH:15]=2)[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1)[CH2:31][CH2:30][S:27]([CH3:26])(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 59837371HCID 59837371, compound

Product 1

HCID 59837356HCID 59837356, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-methyl-1-{4-[4-(3-morpholin-4-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methanamine (230 mg, 0.66 mmol) in methanol (2 mL) was added methanesulfonyl-ethene (64 μL, 0.72 mmol) and the mixture stirred at room temperature for 18 hours. The mixture was concentrated in vacuo and triturated with diethyl ether to give the title compound as a white solid (274 mg, 91%). 1H NMR (400 MHz, CDCl3) δ 1.81 (m, 2H), 1.97 (m, 2H), 2.04 (s, 3H), 2.13 (m, 2H), 2.42-2.58 (m, 8H), 2.62 (t, 2H), 2.74 (s, 3H), 2.81 (t, 2H), 3.50 (m, 2H), 3.70-3.80 (m, 6H), 4.00 (t, 2H), 6.86 (d, 2H), 7.20 (d, 2H). HRMS ESI+ m/z 455.2570 [MH]+. Microanalysis: Found: C, 60.61; H, 8.47; N, 6.09%. C23H38N2O5S requires C, 60.76; H, 8.42; N, 6.16%.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-60216feac4c84c39b3a266177f52709a
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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