HCID 44474165, compound → HCID 44474166, compound

HRID 889606Notes

Reaction equation

HRID 889606 reaction equation
[CH:1]1([CH2:6][CH:7]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)[C:8]([NH:10][C:11]2[S:12][C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[C:15]([O:20][CH3:21])[N:14]=3)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.C(O)(=O)C.[Fe]>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([CH:7]([CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:8]([NH:10][C:11]2[S:12][C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[C:15]([O:20][CH3:21])[N:14]=3)=[O:9])=[CH:23][CH:24]=1

Participants

5

Reactant 1

HCID 44474165HCID 44474165, compound

Product 1

HCID 44474166HCID 44474166, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The title C compound, 3-cyclopentyl-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-2-(4-nitro-phenyl)-propionamide (12 g, 28.2 mmol) is diluted with 160 mL of ethanol and 150 mL acetic acid. 8 g of iron powder (325 mesh, 0.14 mol) is added and the mixture heated to reflux. Once reflux begins the mixture is stirred vigorously and then heating is discontinued and the mixture is allowed to cool slowly. The solvents are removed and the residue is treated with 250 mL of water. Saturated sodium bicarbonate is added carefully to bring the mixture to a pH of 8-9. The mixture is extracted with ethyl acetate, washed with brine, dried and evaporated to give an orange solid which is triturated from hexane. The resulting solid is collected by filtration to afford 2-(4-amino-phenyl)-3-cyclopentyl-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-propionamide: 1H NMR (400 MHz, CDCl3) δ 1.0-1.1 (m, 2H), 1.4-1.8 (m, 5H), 1.8-1.9 (m, 2H), 2.1-2.25 (m, 2H), 3.6 (t, 1H, J=7.8), 3.98 (s, 3H), 6.7 (d, 1H, J=8.8), 6.8 (d, 2H, J=8.6), 7.2 (d, 2H, J=8.6), 7.8 (d, 1H, J=8.8); LC/MS 397 (M+1).

Workup

  1. temperaturethe mixture heated to reflux
  2. temperatureOnce reflux
  3. temperatureheating
  4. temperatureto cool slowly
  5. customThe solvents are removed
  6. additionthe residue is treated with 250 mL of water
  7. additionSaturated sodium bicarbonate is added carefully
  8. extractionThe mixture is extracted with ethyl acetate
  9. washwashed with brine
  10. customdried
  11. customevaporated
  12. customto give an orange solid which
  13. customis triturated from hexane
  14. filtrationThe resulting solid is collected by filtration

Sources & evidence

ORD record
ord-54f04ef3e49844c898eb746cbd7334ee
Source dataset
uspto-grants-2012_08
Patent number
US08252931B2

Reaction notes

Loading…