Ethane, 2-bromo-1,1-diethoxy- → HCID 66816955, compound

HRID 1754960Notes

Reaction equation

HRID 1754960 reaction equation
[CH2:1](OC(OCC)CBr)[CH3:2].[CH3:10][C:11]1[CH:12]=[C:13]([N:41]([CH3:45])[C:42]([NH2:44])=[S:43])[CH:14]=[C:15]([CH3:40])[C:16]=1[CH2:17][CH2:18][S:19]([N:22]1[CH2:39][CH2:38][C:25]2([N:29]=[C:28]([CH:30]3[CH2:35][CH2:34][CH:33]([CH3:36])[CH2:32][CH2:31]3)[NH:27][C:26]2=[O:37])[CH2:24][CH2:23]1)(=[O:21])=[O:20]>C(O)(=O)C>[CH3:10][C:11]1[CH:12]=[C:13]([N:41]([CH3:45])[C:42]2[S:43][CH:1]=[CH:2][N:44]=2)[CH:14]=[C:15]([CH3:40])[C:16]=1[CH2:17][CH2:18][S:19]([N:22]1[CH2:39][CH2:38][C:25]2([N:29]=[C:28]([CH:30]3[CH2:31][CH2:32][CH:33]([CH3:36])[CH2:34][CH2:35]3)[NH:27][C:26]2=[O:37])[CH2:24][CH2:23]1)(=[O:20])=[O:21]

Participants

4

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 86672764HCID 86672764, compound

Product 1

HCID 66816955HCID 66816955, compoundYield 6.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromoacetaldehyde diethylacetal (44.2 mg, 0.224 mmol) was added to a solution of 1-(3,5-dimethyl-4-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-phenyl)-1-methyl-thiourea (100 mg, 0.187 mmol) in acetic acid (2 ml) in a nitrogen stream. The mixture was heated under reflux for two hours and then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, and the organic layer was then sequentially washed with a saturated aqueous sodium bicarbonate solution and saturated brine and dried over anhydrous magnesium sulfate. The organic layer was concentrated, and the resulting residue was then purified by silica gel column chromatography (dichloromethane-methanol) to give 8-{2-[2,6-Dimethyl-4-(methyl-thiazol-2-yl-amino)-phenyl]-ethanesulfonyl}-2-(4-methyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (7.1 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for two hours
  3. concentrationconcentrated under reduced pressure
  4. additionThe resulting residue was diluted with dichloromethane
  5. washthe organic layer was then sequentially washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe organic layer was concentrated
  8. customthe resulting residue was then purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-a50678a31f024377980bcba6eb58f452
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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