Hydrochloric Acid → 3-((8-(3-(1H-Benzo[d][1,2,3]triazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 1751035Notes

Reaction equation

HRID 1751035 reaction equation
[N:1]1([CH2:10][CH2:11][CH2:12][N:13]2[CH2:43][CH2:42][C:16]3([N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][N:18]([CH2:27][C:28]4[CH:29]=[C:30]([CH:38]=[CH:39][CH:40]=4)[C:31]([O:33]C(C)(C)C)=[O:32])[C:17]3=[O:41])[CH2:15][CH2:14]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.Cl>O1CCOCC1>[N:1]1([CH2:10][CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][C:16]3([N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][N:18]([CH2:27][C:28]4[CH:29]=[C:30]([CH:38]=[CH:39][CH:40]=4)[C:31]([OH:33])=[O:32])[C:17]3=[O:41])[CH2:42][CH2:43]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58046660HCID 58046660, compound

Product 1

HCID 580467483-((8-(3-(1H-Benzo[d][1,2,3]triazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 3-((8-(3-(1H-benzo[d][1,2,3]triazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.21 g, 0.34 mmol) was added 4M solution of HCl in dioxane (3 mL). After stirring at room temperature for 3 hours, the reaction mixture was concentrated in vacuo and lyophilized in acetonitrile/water (1:1) to obtain the title compound as a hydrochloride salt (0.2 g, 99%); 1H NMR (DMSO-d6): δ 1.89 (d, 2H, J=14.8 Hz), 2.49-2.51 (m, 2H), 2.95-3.03 (m, 2H), 3.22-3.27 (m, 2H), 3.53-3.69 (m, 4H), 4.64 (d, 4H, J=4 Hz), 4.86 (t, 2H, J=7.2 Hz), 6.78 (t, 1H, J=7.2 Hz), 7.04 (d, 2H, J=8 Hz), 7.20 (t, 2H, J=7.2 Hz), 7.41-7.61 (m, 4H), 7.86-7.89 (m, 2H), 7.97 (d, 1H, J=8.4 Hz), 8.07 (d, 1H, J=8.8 Hz), 10.94 (br, 1H), 13.03 (br, 1H); MS for C30H32N6O3 m/z 525.08 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f1b3318a383e4dca981dd49bd1925f6d
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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