HCID 86676259, compound → HCID 71237051, compound

HRID 1045796Notes

Reaction equation

HRID 1045796 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:17]2[N:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]2[CH:22]=[CH:23][CH:24]=[CH:25][C:14]=2[C:13](=[N:26]O)[C:12]1=[O:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>[Ni].O1CCCC1>[NH2:26][CH:13]1[C:14]2[CH:25]=[CH:24][CH:23]=[CH:22][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[N:18][C:17]=2[N:11]([CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3])[C:12]1=[O:28]

Participants

5

Reactant 2

HCID 86676259HCID 86676259, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71237051HCID 71237051, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
62.5 °C

Procedure

Combine 5-[2-(tert-butyl(dimethyl)silyl)oxyethyl]-7-hydroxyimino-pyrido[2,3-d][3]benzazepin-6-one (206.0 g, 0.52 mol) and tetrahydrofuran (2.3 L) into an autoclave under an atmosphere of nitrogen. Add Raney nickel (232.0 g, 1.13 wt/wt equivalents) to the reaction mixture and introduce hydrogen atmosphere (87 psi). Stir the reaction mixture at 60-65° C. for 24 hours. Filter the mixture over diatomaceous earth and wash the filter aid with tetrahydrofuran (500 mL). Concentrate the filtrate to obtain the title compound (196.0 g, 93.2%) as a brown oil. MS (m/z): 384 (M+1).

Workup

  1. filtrationFilter the mixture over diatomaceous earth
  2. washwash the filter aid with tetrahydrofuran (500 mL)
  3. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-f731c526a8574e6c956ef9a19a7cb125
Source dataset
uspto-grants-2013_10
Patent number
US08569286B2

Reaction notes

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