Methylamine → HCID 68721249, compound

HRID 1875258Notes

Reaction equation

HRID 1875258 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([S:24](Cl)(=[O:26])=[O:25])[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH3:28][NH2:29]>CC(C)=O.C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([S:24]([NH:29][CH3:28])(=[O:26])=[O:25])[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 86761669HCID 86761669, compound

Product 1

HCID 68721249HCID 68721249, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-2-sulfonyl chloride (0.341 g, 0.72 mmol) in acetone (4.5 mL) and THF (2.5 mL) was added to a 0° C. solution of methylamine (3.6 mL of a 2M solution in THF, 7.2 mmol) in THF (2 mL). The reaction mixture was stirred at RT for 1 h and evaporated. The residue was taken up in EtOAc and washed with brine. The organic phase was dried (Na2SO4), filtered evaporated, and purified by silica gel chromatography (0-25% EtOA/hexanes) to give the title compound (0.23 g, 68%) as a light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.85 (br. s., 1H), 5.73 (s, 2H), 4.75 (s, 2H), 3.59-3.68 (m, 2H), 2.86 (d, J=5.1 Hz, 3H), 0.93 (d, J=8.4 Hz, 2H), 0.89 (s, 9H), 0.10 (s, 6H), −0.01 (s, 9H).

Workup

  1. customevaporated
  2. washwashed with brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel chromatography (0-25% EtOA/hexanes)

Sources & evidence

ORD record
ord-19712b58f85e432bbcedccfb63f0f2ff
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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