2-Aminopyridine → HCID 44234339, compound

HRID 391278Notes

Reaction equation

HRID 391278 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[O:8]1[CH2:14][CH2:13][C:12]([C:15](Cl)=[O:16])=[CH:11][C:10]2[CH:18]=[CH:19][CH:20]=[CH:21][C:9]1=2>O1CCCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:15]([C:12]1[CH2:13][CH2:14][O:8][C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[CH:11]=1)=[O:16]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 866497862,3-Dihydro-benzo[b]oxepine-4-carbonylchloride

Product 1

HCID 44234339HCID 44234339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 ml of 2-aminopyridine were dissolved in 10 ml thetrahydrofurane. 2,3-Dihydro-benzo[b]oxepine-4-carbonylchloride (1.1 mmol) dissolved in 2 ml tetrahydrofurane were added dropwise. The reaction mixture was quenched by water and extracted with diethylether. The diethylether phase was washed by 1 mol/l sodiumhydroxide and dried over sodiumsulfate. Evaporation of the solvent yielded 230 mg of crude product which was purified by preparative HPLC (Chromolith prep. RP18, Solvent A water:acetonitrile 90:10+0.1% formic acid, solvent B: water:acetonitrile 10:90+0.1% formic acid, flow: t=0 min 25 ml/min, t=1 min 50 ml/min, gradient: t=0 min 10% B, t=1 min 10% B, t=2 min 10% B, t=2.2 min 20% B, t=7.5 min 50% B, t=7.6 min 100% B, t=8.5 min 100% B). Form this 85 mg of 2,3-Dihydro-benzo[b]oxepine-4-carboxylic acid pyridin-2-ylamide. LC-MS 1.6 min, 267.2 (MH+) 1H-NMR: (DMSO-d6, 500 MHz) d [ppm] 10.358 (s, 1H), 8.370 (m, 1H, J=1 Hz), 8.109 (m, 1H, J=4 Hz), 7.815 (m, 1H, J=2.4 Hz), 7.474 (m, 1H, J=2.3 Hz), 7.392 (s, 1H), 7.277 (m, 1H, J=1.7 Hz), 7.140 (m, 1H, J=1.9 Hz), 7.068 (m, 1H, J=3.2 Hz), 6.983 (m, 1H, J=1.9 Hz), 4.259 (m, 2H, J=3.1 Hz), 2.985 (m, 2H, J=2.6 Hz)

Workup

  1. additionwere added dropwise
  2. customThe reaction mixture was quenched by water
  3. extractionextracted with diethylether
  4. washThe diethylether phase was washed by 1 mol/l sodiumhydroxide
  5. dry with materialdried over sodiumsulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6d73ec36165149d882de5e0d55d3f589
Source dataset
uspto-grants-2013_02
Patent number
US08383838B2

Reaction notes

Loading…