Hydrochloric Acid → HCID 66571722, compound

HRID 1851721Notes

Reaction equation

HRID 1851721 reaction equation
[ClH:1].[F:2][C:3]([F:32])=[CH:4][CH:5]1[N:9](C(OCC)=O)[C:8](=[O:15])[N:7]([CH2:16][C:17]2[N:24]3[C:20]([S:21][C:22]([CH2:25][O:26]C)=[N:23]3)=[N:19][C:18]=2[C:28]([F:31])([F:30])[F:29])[CH2:6]1>>[Cl:1][C:3]([F:32])([F:2])[CH2:4][CH:5]1[CH2:6][N:7]([CH2:16][C:17]2[N:24]3[C:20]([S:21][C:22]([CH2:25][OH:26])=[N:23]3)=[N:19][C:18]=2[C:28]([F:31])([F:30])[F:29])[C:8](=[O:15])[NH:9]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 70979962HCID 70979962, compound

Product 1

HCID 66571722HCID 66571722, compoundYield 12%

Conditions

Temperature
100 °C

Procedure

HCl (37%, 4 ml) is added to ethyl 5-(2,2-difluoroethenyl)-3-{[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}-2-oxoimidazolidine-1-carboxylate a22 (226 mg, 0.48 mmol) at room temperature then stirred at 100° C. for 60 h. After cooling and neutralization by sodium carbonate, the reaction mixture is extracted with CH2Cl2 (2×30 ml), dried over MgSO4, filtered and condensed under reduced pressure. The residue is purified by chromatography (basic conditions; gradient; eluent: H2O/CH3CN/NH4CO3/NH4OH 95/5/0.1/0.005 to 40/60/0.1/0.005; 7 min) to afford 25 mg of pure 4-(2-chloro-2,2-difluoroethyl)-1-{[2-(hydroxymethyl)-6-(trifluoromethyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl}imidazolidin-2-one 18.

Workup

  1. temperatureAfter cooling
  2. extractionneutralization by sodium carbonate, the reaction mixture is extracted with CH2Cl2 (2×30 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customcondensed under reduced pressure
  6. customThe residue is purified by chromatography (basic conditions; gradient; eluent: H2O/CH3CN/NH4CO3/NH4OH 95/5/0.1/0.005 to 40/60/0.1/0.005; 7 min)

Sources & evidence

ORD record
ord-325aae3ddf904eaf9ad9b1fc49ba3459
Source dataset
uspto-grants-2015_02
Patent number
US08957218B2

Reaction notes

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