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

HRID 1751057Notes

Reaction equation

HRID 1751057 reaction equation
[CH:1]1([N:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:6]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:46][CH2:45][C:19]4([N:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][N:21]([CH2:30][C:31]5[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=5)[C:34]([O:36]C(C)(C)C)=[O:35])[C:20]4=[O:44])[CH2:18][CH2:17]3)[C:5]2=[O:47])[CH2:3][CH2:2]1.Cl>O1CCOCC1.C([SiH](CC)CC)C>[CH:1]1([N:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:6]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:46][CH2:45][C:19]4([N:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][N:21]([CH2:30][C:31]5[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=5)[C:34]([OH:36])=[O:35])[C:20]4=[O:44])[CH2:18][CH2:17]3)[C:5]2=[O:47])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58046663tert-butyl 3-((8-(3-(3-cyclopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 580467343-((8-(3-(3-Cyclopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-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-cyclopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.27 g, 0.42 mmol) was added 4M solution of HCl in dioxane (4 mL) and triethylsilane (0.1 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 (0.215 g, 83%); 1H NMR (DMSO-d6): δ 0.88-0.90 (m, 2H), 1.01-1.06 (m, 2H), 1.90 (d, 2H, J=14.4 Hz), 2.12 (br, 2H), 2.87-2.91 (m, 3H), 3.21 (br, 2H), 3.45-3.69 (m, 4H), 3.90 (t, 2H, J=7.2 Hz), 4.64 (d, 4H, J=4.4 Hz), 6.80 (t, 1H, J=7.2 Hz), 7.00 (d, 2H, J=8.4 Hz), 7.07-7.09 (m, 2H), 7.19-7.28 (m, 4H), 7.48-7.57 (m, 2H), 7.88 (d, 2H, J=7.2 Hz), 10.33 (br, 1H), 13.02 (br, 1H); MS for C34H37N5O4 m/z 580.13 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-887e06557c934c2fa21327886ca5b179
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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