2-Aminopyridine → HCID 15888360, compound

HRID 1953157Notes

Reaction equation

HRID 1953157 reaction equation
Br[C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>ClCCl>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][N:3]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 10198942HCID 10198942, compound

Product 1

HCID 15888360HCID 15888360, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of 3-bromo-1,2,4-thiadiazolo[4,5-a]benzimidazole (0.30 g, 1.17 mmol) in 15 mL of dichloromethane, 2-aminopyridine (0.276 g, 2.93 mmol) was added dropwise and the mixture was allowed to stir for 48 h. The reaction mixture wad diluted with 100 mL of dichloromethane and washed with water (2×30 mL) and then brine (1×25 mL). The organic layer was dried over magnesium sulfate and evaporated to give a yellow solid (0.26 g, 83%) 1H-NMR (CDCl3)δ 6.59 (apparent 5, 1H, pyr-H), 7.12 (apparent br. d, 1H, pyr-H), 7.28 (t, 1H, ArH), 7.38 (t, 1H, ArH), 7.51 (m, 2H, ArH & pyr-H), 7.70 (d, 1H, ArH), 8.28 (d, 1H, pyr-H); m.p. 155.5-157° C.

Workup

  1. washwashed with water (2×30 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-e76719c36382419db30263ba82df6d57
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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