Hydrochloric Acid → (S)-1-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-3-piperidin-3-ylmethyl-urea Hydrochloride

HRID 896560Notes

Reaction equation

HRID 896560 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH2:14][NH:15][C:16]([NH:18][C:19]2[CH:24]=[C:23]([C:25]3[N:29]([CH3:30])[N:28]=[N:27][N:26]=3)[CH:22]=[C:21]([CH2:31][CH3:32])[CH:20]=2)=[O:17])[CH2:9]1)=O)(C)(C)C.[ClH:33].O1CCOCC1>C(OCC)(=O)C>[ClH:33].[CH2:31]([C:21]1[CH:20]=[C:19]([NH:18][C:16]([NH:15][CH2:14][C@H:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[O:17])[CH:24]=[C:23]([C:25]2[N:29]([CH3:30])[N:28]=[N:27][N:26]=2)[CH:22]=1)[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69736969(S)-3-{3-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-ureidomethyl}-piperidine-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 20814990(S)-1-[3-Ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-3-piperidin-3-ylmethyl-urea HydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-3-{3-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-ureidomethyl}-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 450 μmol) in ethyl acetate (5 mL) was treated with a solution of hydrogen chloride in dioxane (4.0 N, 2 mL, 8 mmol) and stirred at room temperature for 6 hours. The mixture was concentrated, and the residue was triturated twice in diethyl ether and dried under vacuum to provide a white powder (165 mg, 97%). 1H NMR (300 MHz, DMSO-d6) δ9.24 (s, 1H), 8.89 (bm, 1H), 8.68 (bm, 1H), 7.81 (s, 1H), 7.43 (s, 1H), 7.22 (s, 1H), 6.79 (t, J=6 Hz, 1H), 4.16 (s, 3H), 3.40 (m, 2H), 3.20 (m, 2H), 3.05 (m, 2H), 2.9-2.5 (m, 4H), 2.0-1.6 (m, 4H), 1.21 (t, J=8 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated twice in diethyl ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-90e3eb86070c45fca6efaa052237037e
Source dataset
uspto-grants-2005_07
Patent number
US06919356B2

Reaction notes

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