tert-butyl 4-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-8-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-8-yl)-tetrahydropyridine-1(2H)-carboxylate

HRID 708259Notes

Reaction equation

HRID 708259 reaction equation
[CH3:1][C:2]1([CH3:36])[N:6]([C:7]2[S:8][C:9]3[CH2:15][CH2:14][O:13][C:12]4[CH:16]=[C:17]([C:20]5[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]=5)[CH:18]=[CH:19][C:11]=4[C:10]=3[N:33]=2)[C:5](=[O:34])[NH:4][C:3]1=[O:35]>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:36])[N:6]([C:7]2[S:8][C:9]3[CH2:15][CH2:14][O:13][C:12]4[CH:16]=[C:17]([CH:20]5[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:24][CH2:25]5)[CH:18]=[CH:19][C:11]=4[C:10]=3[N:33]=2)[C:5](=[O:34])[NH:4][C:3]1=[O:35]

Participants

4

Reactant 1

HCID 58203717tert-butyl 4-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-8-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 58204137tert-butyl 4-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-8-yl)-tetrahydropyridine-1(2H)-carboxylateYield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl 4-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-8-yl)-5,6-dihydropyridine-1(2H)-carboxylate (48 mg, 0.094 mmol) in 6 ml of ethanol was hydrogenated at 1 atm over 50 mg of 10% palladium on charcoal for 18 hours. The mixture was filtered through celite and concentrated in vacuum giving 49 mg (100%) of tert-butyl 4-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-8-yl)-tetrahydropyridine-1(2H)-carboxylate. MS(ESI+): 513.3

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-4e7c0a2d93e741959512b87d02d50066
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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