Triethylamine → 5-(4-(4-((6-(1H-Tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-ylsulfonyl)-2,4-dimethylthiazole

HRID 80653Notes

Reaction equation

HRID 80653 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[N:12]=[C:11]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH:25]=[N:24][N:23]=[N:22]4)=[N:19][CH:20]=3)[CH:10]=[N:9]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:33][C:34]1[S:35][C:36]([S:40](Cl)(=[O:42])=[O:41])=[C:37]([CH3:39])[N:38]=1>ClCCl>[N:21]1([C:18]2[N:19]=[CH:20][C:15]([O:14][CH2:13][C:11]3[CH:10]=[N:9][N:8]([CH:5]4[CH2:4][CH2:3][N:2]([S:40]([C:36]5[S:35][C:34]([CH3:33])=[N:38][C:37]=5[CH3:39])(=[O:42])=[O:41])[CH2:7][CH2:6]4)[N:12]=3)=[CH:16][CH:17]=2)[CH:25]=[N:24][N:23]=[N:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2776248Dimethyl-1,3-thiazole-5-sulfonyl chlorideHCID 687466245-((2-(piperidin-4-yl)-2H-1,2,3-triazol-4-yl)methoxy)-2-(1H-tetrazol-1-yl)pyridine hydrochloride2×

Product 1

HCID 251742695-(4-(4-((6-(1H-Tetrazol-1-yl)pyridin-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-ylsulfonyl)-2,4-dimethylthiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-((2-(piperidin-4-yl)-2H-1,2,3-triazol-4-yl)methoxy)-2-(1H-tetrazol-1-yl)pyridine hydrochloride (Intermediate 15, 0.050 g, 0.153 mmol), dichloromethane (1.5 mL), and triethyl amine (0.043 mL, 0.306 mmol) was added 2,4-dimethyl-thiazole -5-sulfonyl chloride (0.049 g, 0.229 mmol) and the reaction stirred at room temperature for 2 hours. The solution was concentrated and purified by flash column chromatography on silica gel eluting with 0-100% ethyl acetate in hexanes to afford the desired product.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by flash column chromatography on silica gel eluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7bae3688f70748e4b189aca01c1d0835
Source dataset
uspto-grants-2014_09
Patent number
US08846675B2

Reaction notes

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