tert-butyl 4-(2-(1-((2-(trimethylsilyl)ethoxy)carbonyl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(2-(1-((2-(trimethylsilyl)ethoxy)carbonyl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate

HRID 1429578Notes

Reaction equation

HRID 1429578 reaction equation
[CH3:1][Si:2]([CH3:38])([CH3:37])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]=4)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7]>C(OCC)(=O)C.[Pd]>[CH3:1][Si:2]([CH3:37])([CH3:38])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([CH:24]4[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:26][CH2:25]4)[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7]

Participants

4

Reactant 1

HCID 67464645tert-butyl 4-(2-(1-((2-(trimethylsilyl)ethoxy)carbonyl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 67462856Tert-butyl 4-(2-(1-((2-(trimethylsilyl)ethoxy)carbonyl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylateYield 69.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 4-(2-(1-((2-(trimethylsilyl)ethoxy)carbonyl)-piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (555 mg, 0.991 mmol) in ethyl acetate (10 mL) was added Pd/C (10%, 2.638 g, 2.48 mmol). The mixture was charged with a balloon of H2 and stirred at rt overnight. The reaction mixture was filtered through a pad of celite and rinsed with EtOAc. The filtrate was concentrated to afford tert-butyl 4-(2-(1-((2-(trimethylsilyl)ethoxy)carbonyl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)piperidine-1-carboxylate (385 mg, 0.685 mmol, 69% yield) as a gray gum. LCMS (m/z)=562 (M+H)+.

Workup

  1. additionThe mixture was charged with a balloon of H2
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washrinsed with EtOAc
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b90ab6d151a84e09b6e4a825a294486c
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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