Ethanol → HCID 86726669, compound

HRID 1499417Notes

Reaction equation

HRID 1499417 reaction equation
[N+:1]([C:4]1[C:5]([N:22]2[CH2:27][CH2:26][CH2:25][C@H:24]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23]2)=[C:6]2[CH:12]=[CH:11][N:10]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:7]2=[N:8][CH:9]=1)([O-])=O.[NH4+].[Cl-].CCO>[Fe].O>[NH2:1][C:4]1[C:5]([N:22]2[CH2:27][CH2:26][CH2:25][C@H:24]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:23]2)=[C:6]2[CH:12]=[CH:11][N:10]([S:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)(=[O:15])=[O:14])[C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 86726668HCID 86726668, compound

Product 1

HCID 86726669HCID 86726669, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a vial containing tert-butyl {(3S)-1-[5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-3-yl}carbamate (719.5 mg, 1.434 mmol), iron powder (793.6 mg, 14.21 mmol) and NH4Cl (1147.6 mg, 21.454 mmol), EtOH (10.00 mL) was added followed by water (2.00 mL). The mixture was stirred at 80° C. for 2 h. The reaction mixture was then filtered through a pad of diatomaceous earth. The pad was eluted with 10% aq. K3PO4 (50 mL) and EtOAc (50 mL). The organic layer was washed with brine (50 mL), then dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a dark solid (491.8 mg, 73%). LCMS calc. for C23H30N5O4S (M+H)+: m/z=472.2. found 472.2.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was then filtered through a pad of diatomaceous earth
  3. washThe pad was eluted with 10% aq. K3PO4 (50 mL) and EtOAc (50 mL)
  4. washThe organic layer was washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-97e215fd2c744818880fac208fc8a19d
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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