Hydrochloric Acid → HCID 66652432, compound

HRID 1750936Notes

Reaction equation

HRID 1750936 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[N:10]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9]1.Cl>O1CCOCC1>[O:13]=[C:12]1[C:11]2([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[N:10]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][N:8]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66652294HCID 66652294, compound

Product 1

HCID 66652432HCID 66652432, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 3-(5-methoxy-5-oxopentyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.09 g, 0.2 mmol) was added 4M solution of HCl in dioxane (1 mL). After stirring at room temperature for 2 hours, the reaction mixture was concentrated in vacuo to obtain methyl 5-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)pentanoate as a hydrochloride salt. To a solution of the hydrochloride salt and potassium carbonate (0.069 g, 0.5 mmol) in N,N-dimethylformamide (2 mL), was added 1-(3-iodopropyl)-1,3-dihydro-2H-benzimidazol-2-one (0.06 g, 0.2 mmol). After stirring at 55° C. for 18 hours, the reaction mixture was diluted with ethyl acetate (25 mL), washed with water and brine. The organic phase was dried over MgSO4, filtered, concentrated and isolated by pTLC (10% methanol/dichloromethane) to obtain the product (0.05 g, 48%); 1H NMR (DMSO-d6): δ 1.50-1.57 (m, 6H), 1.81 (br, 2H), 2.32-2.36 (m, 4H), 2.60-2.67 (m, 8H), 3.57 (s, 3H), 3.84 (t, 2H, J=6.8 Hz), 4.64 (s, 2H), 6.77 (t, 1H, J=7.2 Hz), 6.88 (d, 2H, J=8 Hz), 6.96 (d, 3H, J=3.2 Hz), 7.17-7.19 (m, 1H), 7.25 (t, 2H, J=8.4 Hz), 10.8 (s, 1H); MS for C29H37N5O4 m/z 520.11 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d245dab91c2f460a87d0d3f476694251
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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