Hydrochloric Acid → 3-((8-(3-(3,3-Dimethyl-2-oxoindolin-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 1751059Notes

Reaction equation

HRID 1751059 reaction equation
[CH3:1][C:2]1([CH3:47])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][N:14]2[CH2:45][CH2:44][C:17]3([N:21]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH2:20][N:19]([CH2:29][C:30]4[CH:31]=[C:32]([CH:40]=[CH:41][CH:42]=4)[C:33]([O:35]C(C)(C)C)=[O:34])[C:18]3=[O:43])[CH2:16][CH2:15]2)[C:3]1=[O:46].Cl>O1CCOCC1.C([SiH](CC)CC)C>[CH3:1][C:2]1([CH3:47])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][N:14]2[CH2:45][CH2:44][C:17]3([N:21]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH2:20][N:19]([CH2:29][C:30]4[CH:31]=[C:32]([CH:40]=[CH:41][CH:42]=4)[C:33]([OH:35])=[O:34])[C:18]3=[O:43])[CH2:16][CH2:15]2)[C:3]1=[O:46]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58046669Tert-butyl 3-((8-(3-(3,3-dimethyl-2-oxoindolin-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 580467413-((8-(3-(3,3-Dimethyl-2-oxoindolin-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 12052TriethylsilaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 3-((8-(3-(3,3-dimethyl-2-oxoindolin-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.16 g, 0.25 mmol) was added 4M solution of HCl in dioxane (2.5 mL) and triethylsilane (0.05 mL). After stirring at room temperature for 4 hours, the reaction mixture was concentrated in vacuo and lyophilized in acetonitrile/water (1:1) to obtain the title compound as a hydrochloride salt (0.14 g, 90%); 1H NMR (DMSO-d6): δ 1.28 (s, 6H), 1.91 (d, 2H, J=14 Hz), 2.07 (br, 2H), 2.71 (t, 2H, J=10 Hz), 3.17 (br, 2H), 3.45-3.71 (m, 4H), 3.76 (t, 2H, J=7.2 Hz), 4.62 (s, 4H), 7.04-7.07 (m, 5H), 7.15 (d, 1H, J=7.6 Hz), 7.27 (t, 1H, J=8 Hz), 7.36 (d, 1H, J=7.6 Hz), 7.50 (t, 1H, J=8 Hz), 7.55 (d, 1H, J=7.6 Hz), 7.87 (dd, 2H, J=6.8 and 1.6 Hz), 10.39 (br, 1H), 13.03 (br, 1H); MS for C34H37FN4O4 m/z 585.23 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-622463a26f9c424ab95c39e7e9e56e93
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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