Water → HCID 178474505, compound

HRID 1992562Notes

Reaction equation

HRID 1992562 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.[C:29](Cl)(=[O:31])[CH3:30].O>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]\[C:29](=[O:31])[CH3:30])[S:8][CH:9]=2)=[CH:19][CH:18]=1)#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 247845394-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile

Product 1

HCID 178474505HCID 178474505, compoundYield 64.6%

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 (0.075 g, 0.25 mmol), prepared in Example 4, was dissolved in tetrahydrofuran (2 mL) followed by triethylamine (0.069 mL, 0.5 mmol) and acetylchloride (0.039 g, 0.5 mmol). The mixture was stirred 4 h, poured into water, extracted with ethyl acetate, and dried over anhydrous MgSO4. The solvent was evaporated and residue triturated with hexane/ethyl acetate (95/5), collected and dried to give the title compound (0.055 g, 64%). HRMS: calcd for C17H16N4O2S+H+, 341.10667; found (ESI, [M+H]+), 341.1075; HPLC purity 96.5% at 210-370 nm, 9.4 min.; 96.0% at 250 nm, 9.4 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. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous MgSO4
  3. customThe solvent was evaporated
  4. customresidue triturated with hexane/ethyl acetate (95/5)
  5. customcollected
  6. customdried

Sources & evidence

ORD record
ord-68ef91dea4714637843bd81cced1a8fd
Source dataset
uspto-grants-2010_01
Patent number
US07649007B2

Reaction notes

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