Diisopropylethylamine → HCID 90010077, compound

HRID 1056605Notes

Reaction equation

HRID 1056605 reaction equation
BrC1C=[C:4]([C:10]2[O:14]C(=O)NN=2)C=NC=1CC.[Br:16][C:17]1[C:18]([CH2:27][CH3:28])=[N:19][CH:20]=[C:21]([CH:26]=1)[C:22](NN)=[O:23].C(N(C(C)C)CC)(C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:16][C:17]1[C:18]([CH2:27][CH3:28])=[N:19][CH:20]=[C:21]([CH:26]=1)[C:22]([O:14][CH2:10][CH3:4])=[O:23]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 90010191HCID 90010191, compoundHCID 90010446HCID 90010446, compound

Product 1

HCID 90010077HCID 90010077, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Step-3: 5-(5-Bromo-6-ethylpyridin-3-yl)-1,3,4-oxadiazol-2(3H)-one: To a stirred and cooled (0° C.) solution of 5-bromo-6-ethylnicotinohydrazide (2.50 g, 10.24 mmol, 1.0 eq) and diisopropylethylamine (3.58 mL, 20.48 mmol, 2.0 eq) in DCM (20 mL) was added a solution of triphosgene (1.21 g, 4.10 mmol, 0.4 eq) in DCM (10 mL) over a period of 10 min. The resulting mixture was stirred for 1 h at the same temperature. The reaction mixture was then diluted with DCM (50 mL) and washed with water (50 mL), aqueous sodium bicarbonate (10%, 50 mL), brine (50 mL), dried (Na2SO4) and filtered. The filtrate was evaporated under vacuum to afford 1.60 g (58%) of the desired product as a white solid. 1HNMR (400 MHz, DMSO) δ 8.83 (d, J=1.5 Hz, 1H), 8.25 (d, J=1.5 Hz, 1H), 2.92 (q, J=7.0 Hz, 2H), 1.21 (t, J=7.0 Hz, 3H); ESI-MS (m/z) 270, 272 [(MH)+ Br79, 81].

Workup

  1. washwashed with water (50 mL), aqueous sodium bicarbonate (10%, 50 mL), brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-04c778e5a3d340f5baaa29b28f7c5a37
Source dataset
uspto-grants-2016_07
Patent number
US09399638B2

Reaction notes

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