Triethylamine → (NZ)-N-[3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-4,4-dimethyl-1,3-oxazolidin-2-ylidene]methanesulfonamide

HRID 1436472Notes

Reaction equation

HRID 1436472 reaction equation
[NH:1]=[C:2]1[N:6]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[N:11]=2)[C:5]([CH3:21])([CH3:20])[CH2:4][O:3]1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>O1CCCC1>[C:16]([C:15]1[CH:14]=[CH:13][C:12]([C:10]2[N:11]=[C:7]([N:6]3[C:5]([CH3:21])([CH3:20])[CH2:4][O:3]/[C:2]/3=[N:1]\[S:30]([CH3:29])(=[O:32])=[O:31])[S:8][CH:9]=2)=[CH:19][CH:18]=1)#[N:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 247845394-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile

Product 1

HCID 24784782(NZ)-N-[3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-4,4-dimethyl-1,3-oxazolidin-2-ylidene]methanesulfonamideYield 6.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile (0.250 g, 0.83 mmol), prepared in Example 63, was dissolved in tetrahydrofuran (2 mL), followed by triethylamine (0.139 mL, 1 mmol) and methanesulfonyl chloride (0.154 mL, 2 mmol). The mixture was stirred overnight, filtered and the tetrahydrofuran was removed in vacuo. Purification by normal phase HPLC on a phenomenex cyano column and eluting with hexane/1,2-dimethoxyethane (9:1 to 1:9) gave the title compound (0.020 g, 6%). HRMS: calcd for C16H16N4O3S2+H+, 377.07366; found (ESI, [M+H]+), 377.0722. HPLC purity 97.0% at 210-370 nm, 8.5 min; 97.1% at 244 nm, 8.5 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Workup

  1. filtrationfiltered
  2. customthe tetrahydrofuran was removed in vacuo
  3. customPurification by normal phase HPLC on a phenomenex cyano column
  4. washeluting with hexane/1,2-dimethoxyethane (9:1 to 1:9)

Sources & evidence

ORD record
ord-c7cd2293bea54972882ffe6a60ae13e9
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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