2,2-Dimethoxypropane → HCID 66743494, compound

HRID 2364018Notes

Reaction equation

HRID 2364018 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:9])=[O:8])=[C:4]([NH:10][CH2:11][C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[CH:3]=1.[CH3:20][C:21]1(C)C2(CS(O)(=O)=O)C(C[CH:22]1CC2)=O.COC(OC)(C)C.C([O-])(O)=O.[Na+]>O.CC(N(C)C)=O>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:8])[NH:9][C:21]([CH3:22])([CH3:20])[N:10]([CH2:11][C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[O:13])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 66743991HCID 66743991, compound

Product 1

HCID 66743494HCID 66743494, compoundYield 394.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-3-[(2-(morpholin-4-yl)-2-oxoethyl)amino]thiophene-2-carboxamide (120 mg, 0.345 mmol), CSA (10 mg), 2,2-dimethoxypropane (1.0 mL) and DMA (1 mL) was stirred at 80° C. for 0.5 h. Then, water and saturated aqueous NaHCO3 were added to quench the reaction. The precipitate was collected by filtration to afford the title compound (66 mg) as a pale brown solid. From the filtrate, the organic layer was collected, washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to afford the title compound (50 mg) as a pale brown solid. Total yield of the title compound (66+50 mg) was 87%:

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5d8cadfaa320415791e9c28da8354eaf
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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