Lithium hydroxide, monohydrate → HCID 54771748, compound

HRID 2362913Notes

Reaction equation

HRID 2362913 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][N:21]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[NH:23][C:22]4=[O:30])[CH2:14][CH2:13]3)[C:11](=[O:31])[N:10]([CH2:32][C:33]3[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=3)[C:36]([O:38]C)=[O:37])[CH2:9]2)=[CH:4][CH:3]=1.O.[OH-].[Li+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][N:21]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[NH:23][C:22]4=[O:30])[CH2:14][CH2:13]3)[C:11](=[O:31])[N:10]([CH2:32][C:33]3[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=3)[C:36]([OH:38])=[O:37])[CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66652314HCID 66652314, compound

Product 1

HCID 54771748HCID 54771748, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-((1-(4-fluorophenyl)-4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.25 g, 0.44 mmol) in methanol (3 mL) was added lithium hydroxide monohydrate (0.037 g, 0.88 mmol) in water (1 mL). After stirring at room temperature for 18 h, the reaction mixture was concentrated in vacuo and isolated by reverse phase HPLC to obtain the title compound as an acetate salt (0.05 g, 13%); 1H NMR (DMSO-d6): δ 1.62 (d, 2H, J=13.2 Hz), 1.81 (t, 2H, J=6.4 Hz), 2.27-2.37 (m, 4H), 2.50-2.69 (m, 4H), 3.83 (t, 2H, J=6.8 Hz), 4.56 (d, 4H, J=15.2 Hz), 6.88-6.91 (m, 2H), 6.95-6.98 (m, 3H), 7.08 (d, 2H, J=5.2 Hz), 7.13-7.16 (m, 1H), 7.47-7.52 (m, 2H), 7.85-7.87 (m, 2H), 10.81 (s, 1H), 13.10 (br, 1H); MS for C31H32FN5O4 m/z 558.02 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customisolated by reverse phase HPLC

Sources & evidence

ORD record
ord-23482aeaa2a74b56a3bf259e28745396
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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