Hydrochloric Acid → 1-(4-(4-((6-(1h-Tetrazol-1-yl)pyridin-3-yloxy)methyl)-2h-1,2,3-triazol-2-yl)piperidin-1-yl)-2-(piperidin-4-yl)ethanone hydrochloride

HRID 80666Notes

Reaction equation

HRID 80666 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:18]=[N:17][N:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25](=[O:40])[CH2:26][CH:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)[CH2:21][CH2:20]4)[N:15]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[ClH:41]>ClCCl>[ClH:41].[N:1]1([C:6]2[N:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:18]=[N:17][N:16]([CH:19]4[CH2:20][CH2:21][N:22]([C:25](=[O:40])[CH2:26][CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[CH2:23][CH2:24]4)[N:15]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25174586tert-Butyl 4-(2-(4-(-((6-(1H-tetrazol-1-yl)pyridine-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)-2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 687446381-(4-(4-((6-(1h-Tetrazol-1-yl)pyridin-3-yloxy)methyl)-2h-1,2,3-triazol-2-yl)piperidin-1-yl)-2-(piperidin-4-yl)ethanone hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-(4-(-((6-(1H-tetrazol-1-yl)pyridine-3-yloxy)methyl)-2H-1,2,3-triazol-2-yl)piperidin-1-yl)-2-oxoethyl)piperidine-1-carboxylate (110 mg, 0.20 mmol) in dichloromethane (5 mL) cooled to 0° C. was added hydrochloric acid (4M in 1,4-dioxane, 5 eq.) dropwise. After the reaction was stirred for 3 h the solvents were removed in vacuo to afford the desired HCl salt. 1H NMR (DMSO-d6): δ 10.06 (1H, s), 8.78 (1H, br), 8.40 (1H, d), 7.98 (1H, d), 7.94 (1H, s), 7.87 (1H, dd), 5.35 (2H, s), 4.79 (1H, m), 4.34 (1H, m), 3.92 (1H, m), 3.20 (3H, m), 2.83 (2H, m), 2.31 (2H, d), 2.10 (2H, m), 1.93 (2H, m), 1.77 (3H, m), 1.32 (2H, m).

Workup

  1. customwere removed in vacuo

Sources & evidence

ORD record
ord-04bf3dcf5e174be9921939af08968faf
Source dataset
uspto-grants-2014_09
Patent number
US08846675B2

Reaction notes

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