Cyclopropylamine → HCID 68452900, compound

HRID 2357650Notes

Reaction equation

HRID 2357650 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=O)[S:5][C:6]=1[CH3:7].C([N:14]([CH:17]([CH3:19])[CH3:18])CC)(C)C.C1(N)CC1>S(Cl)(Cl)=O.O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:14][CH:17]2[CH2:19][CH2:18]2)=[O:10])[S:5][C:6]=1[CH3:7]

Participants

7

Reactant 3

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 8188894-Bromo-5-methylthiophene-2-carboxylic acid

Product 1

HCID 68452900HCID 68452900, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

4-Bromo-5-methylthiophene-2-carboxylic acid (1.05 g, 4.75 mmol) was suspended in thionyl chloride (4.75 mL) and heated to 70° C. for 1.5 h. The mixture was concentrated and dried azeotropically with toluene. The reaction mixture was dissolved in dioxane (11.9 mL) to which diisopropylethylamine (4.14 mL, 23.7 mmol) and cyclopropylamine (1.36 mL, 23.7 mmol) were added and stirred at RT for 2 h. The reaction mixture was diluted with 50 mL ethyl acetate, partitioned with sodium bicarbonate (saturated, aqueous), and the organic layers were washed 2×50 mL with sodium bicarbonate (saturated, aqueous), washed with 3 N HCl, separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. MS (ES+): 262 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. dry with materialdried azeotropically with toluene
  3. additionwere added
  4. custompartitioned with sodium bicarbonate (saturated, aqueous)
  5. washthe organic layers were washed 2×50 mL with sodium bicarbonate (saturated, aqueous)
  6. washwashed with 3 N HCl
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fbc042e37a8a4645984f52f97cada694
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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