Triethylamine → 4-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile

HRID 1436467Notes

Reaction equation

HRID 1436467 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][C:10]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:20]=[C:21]([C:25]#[N:26])[N:22]([CH3:24])[CH:23]=2)[N:18]=1)([CH3:12])[CH3:11].Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl.O.C(OCC)(=O)C>O1CCCC1>[CH3:11][C:10]1([CH3:12])[CH2:9][O:8][C:28](=[O:30])[N:13]1[C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:20]=[C:21]([C:25]#[N:26])[N:22]([CH3:24])[CH:23]=2)[N:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 22728543Water ethylacetateHCID 866186224-[2-(2-hydroxy-1,1-dimethyl-ethylamino)-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile

Product 1

HCID 689019664-[2-(4,4-Dimethyl-2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrileYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of triethylamine (0.42 mL, 3 mmol) and 4-[2-(2-hydroxy-1,1-dimethyl-ethylamino)-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile (0.75 g, 2.71 mmol), prepared in the previous step, in dry tetrahydrofuran (10 mL) was added triphosgene (0.83 g, 2.8 mmol) at room temperature. After 16 h, the mixture was poured into water/ethyl acetate. The organic layer was washed with water, dried (anhydrous sodium sulfate) and evaporated. The product was purified by silica gel column chromatography (ethyl acetate:hexanes, 1:4) to afford the title compound (0.29 g, 36%) as a white powder. HRMS: calcd for C14H14N4O2S [M+H]+, 303.09102; found (ESI, [M+H]+), 303.0914; ANLC 99.6% at 210-370 nm, 9.0 min; 99.5% at 260 nm, 9.0 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. washThe organic layer was washed with water
  2. dry with materialdried (anhydrous sodium sulfate)
  3. customevaporated
  4. customThe product was purified by silica gel column chromatography (ethyl acetate:hexanes, 1:4)

Sources & evidence

ORD record
ord-9271670c15374ba7b85ed0ac077ec0ab
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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