Hydrochloric Acid → 3-((4-Oxo-8-(3-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 1751024Notes

Reaction equation

HRID 1751024 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]3[C:20](=[O:21])[CH2:19][O:18][C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]3=4)[CH2:8][CH2:7]2)[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:4][N:3]1[CH2:32][C:33]1[CH:34]=[C:35]([CH:43]=[CH:44][CH:45]=1)[C:36]([O:38]C(C)(C)C)=[O:37].Cl>O1CCOCC1>[O:1]=[C:2]1[C:6]2([CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][N:15]3[C:20](=[O:21])[CH2:19][O:18][C:17]4[CH:22]=[CH:23][CH:24]=[CH:25][C:16]3=4)[CH2:10][CH2:11]2)[N:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:4][N:3]1[CH2:32][C:33]1[CH:34]=[C:35]([CH:43]=[CH:44][CH:45]=1)[C:36]([OH:38])=[O:37]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58046693tert-butyl 3-((4-oxo-8-(3-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 580467253-((4-Oxo-8-(3-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propyl)-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-((4-oxo-8-(3-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.1 g, 0.16 mmol) was added 4M solution of HCl in dioxane (2 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 (0.095 g, 99%); 1H NMR (DMSO-d6): δ 1.92 (d, 2H, J=14 Hz), 2.03-2.07 (m, 2H), 2.85 (t, 2H, J=10 Hz), 3.25 (br, 2H), 3.62-3.72 (m, 4H), 3.99 (t, 2H, J=6.8 Hz), 4.61-4.67 (m, 6H), 6.81 (t, 1H, J=7.6 Hz), 6.96-7.10 (m, 5H), 7.23 (t, 2H, J=7.2 Hz), 7.31 (d, 1H, J=7.6 Hz), 7.48-7.57 (m, 2H), 7.87-7.89 (m, 2H), 9.96 (br, 1H), 13.03 (s, 1H); MS for C32H34N4O5 m/z 555.06 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-bc0ba670764945738b03a4bac34b39da
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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