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

HRID 1429577Notes

Reaction equation

HRID 1429577 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[S:9][C:10]3[CH:16]=[C:15]([C:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]=4)[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:3][CH2:2]1.CCN(CC)CC.[C:37](=O)([O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[O:38]N1C(=O)CCC1=O>O1CCOCC1.C(Cl)Cl>[CH3:50][Si:49]([CH3:52])([CH3:51])[CH2:48][CH2:47][O:46][C:37]([N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[S:9][C:10]3[CH:16]=[C:15]([C:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]=4)[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:3][CH2:2]1)=[O:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 67468425tert-butyl 4-(2-(piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 67464645tert-butyl 4-(2-(1-((2-(trimethylsilyl)ethoxy)carbonyl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(2-(piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (450 mg, 1.083 mmol) in dioxane (10 mL) was added Et3N (0.45 mL, 3.25 mmol) followed by 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate (281 mg, 1.083 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with CH2Cl2 (30 mL), washed with water (30 mL) and brine. The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 35% EtOAc) to afford 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, 92% yield) as a white solid. LCMS (m/z)=560 (M+H)+.

Workup

  1. washwashed with water (30 mL) and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 35% EtOAc)

Sources & evidence

ORD record
ord-5cf561b477c443efa4525e685c0314c5
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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