Ethanol → HCID 86726663, compound

HRID 1499410Notes

Reaction equation

HRID 1499410 reaction equation
[N+:1]([C:4]1[C:5]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.[NH4+].[Cl-].CCO>[Fe].O>[NH2:1][C:4]1[C:5]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:14]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 86726662HCID 86726662, compound

Product 1

HCID 86726663HCID 86726663, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a vial containing tert-butyl [(3S)-1-(6-nitrothieno[3,2-b]pyridin-7-yl)piperidin-3-yl]carbamate (210.1 mg, 0.5552 mmol), iron powder (306.1 mg, 5.481 mmol) and NH4Cl (491.9 mg, 9.196 mmol), EtOH (5.00 mL) was added, followed by water (1.00 mL). The mixture was stirred at 80° C. for 2 h. The reaction mixture was then filtered through a pad of diatomaceous earth. The diatomaceous earth pad was eluted with a 10% aq. K3PO4 (30 mL) and EtOAc (30 mL). The organic layer was washed with brine (30 mL), then dried over Na2SO4, and concentrated under reduced pressure. The resulting residue (197.9 mg) of the sub-title compound was used in the next step without further purification. LCMS calc. for C17H25N4O2S (M+H)+: m/z=349.2. found 349.2.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was then filtered through a pad of diatomaceous earth
  3. washThe diatomaceous earth pad was eluted with a 10% aq. K3PO4 (30 mL) and EtOAc (30 mL)
  4. washThe organic layer was washed with brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue (197.9 mg) of the sub-title compound was used in the next step without further purification

Sources & evidence

ORD record
ord-5f9813d62af64232b15b4609d2f5eb50
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

Loading…