Triethylamine → HCID 66634724, compound

HRID 1911961Notes

Reaction equation

HRID 1911961 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.Br.Br[C:8]1[S:9][C:10]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[N:11][N:12]=1.C(N(CC)CC)C>C(O)C>[CH:1]1([CH2:4][NH:5][C:8]2[S:9][C:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[N:11][N:12]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75646CyclopropanemethanamineHCID 66610136HCID 66610136, compound

Product 1

HCID 66634724HCID 66634724, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
125 °C

Procedure

A suspension of cyclopropylmethanamine (0.528 g, 0.743 mmol), 2-bromo-5-(3-pyridyl)-1,3,4-thiadiazole hydrobromide (0.2 g, 0.619 mmol) and triethylamine (0.3 ml, 2.16 mmol) in ethanol (20 mL) was heated to 125° C. for 42 minutes in a microwave reaction vessel, cooled to room temperature, concentrated under reduced pressure and resuspended in 2:1 saturated aqueous sodium bicarbonate:ethyl acetate (100 mL). The suspension was shaken vigorously and the organic extract collected and washed with water (50 mL) and brine (30 mL) before drying over magnesium sulfate. The solution was concentrated under reduced pressure and purified by silica column chromatography, eluting with a gradient of methanol in ethyl acetate. The slower eluting fraction was concentrated under reduced pressure to afford the title compound as a yellow solid (38 mg, 26%): mp 162-165° C.; IR (ATR) 1573(s), 1549(s), 1464(m), 1063(m) cm−1; 1H NMR (400 MHz, CDCl3) δ 8.97 (d, J=1.6 Hz, 1H), 8.63 (dd, J=4.8, 1.6 Hz, 1H), 8.18 (ddd, J=8.0, 2.2, 1.7 Hz, 1H), 7.38 (ddd, J=8.0, 4.8, 0.7 Hz, 1H), 5.68 (s, 1H), 3.29 (d, J=7.1 Hz, 2H), 1.26-1.09 (m, 1H), 0.72-0.53 (m, 2H), 0.42-0.25 (m, 2H); 13C NMR (101 MHz, CDCl3) δ 170.01, 154.19, 150.61, 147.94, 133.64, 127.47, 123.76, 52.20, 10.76, 3.73; ESIMS m/z 231.8 ([M−H]−).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. extractionthe organic extract
  4. customcollected
  5. washwashed with water (50 mL) and brine (30 mL)
  6. dry with materialbefore drying over magnesium sulfate
  7. concentrationThe solution was concentrated under reduced pressure
  8. custompurified by silica column chromatography
  9. washeluting with a gradient of methanol in ethyl acetate
  10. washThe slower eluting fraction
  11. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-07f3d1ea26fb49c09897d194c8ab14b5
Source dataset
uspto-grants-2013_12
Patent number
US08604211B2

Reaction notes

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