HCID 58046714, compound → HCID 58046735, compound

HRID 2362972Notes

Reaction equation

HRID 2362972 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][N:14]3[CH2:44][CH2:43][C:17]4([N:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:20][N:19]([CH2:28][C:29]5[CH:30]=[C:31]([CH:39]=[CH:40][CH:41]=5)[C:32]([O:34]C(C)(C)C)=[O:33])[C:18]4=[O:42])[CH2:16][CH2:15]3)[C:6]=2[CH:45]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH2:11][CH2:12][CH2:13][N:14]3[CH2:44][CH2:43][C:17]4([N:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:20][N:19]([CH2:28][C:29]5[CH:30]=[C:31]([CH:39]=[CH:40][CH:41]=5)[C:32]([OH:34])=[O:33])[C:18]4=[O:42])[CH2:16][CH2:15]3)[C:6]=2[CH:45]=1

Participants

4

Reactant 1

HCID 58046714HCID 58046714, compound

Product 1

HCID 58046735HCID 58046735, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3-((8-(3-(6-chloro-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 (100 mg, 0.16 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 4 h. The mixture was concentrated in vacuo and the crude residue was purified using preparatory high performance liquid chromatography to afford the acetate salt of the title compound as a white solid (22 mg, 24%); 1H NMR (400 MHz, DMSO-d6): 1.61 (d, 2H, J=13.2 Hz); 1.83 (t, 2H, J=6.8 Hz); 2.37 (t, 2H, J=7.2 and 6.8 Hz); 2.54-2.58 (m, 2H); 2.67-2.72 (m, 4H); 3.85 (t, 2H, J=6.8 Hz); 4.58 (s, 2H); 4.61 (s, 2H); 6.77 (t, 1H, J=7.6 and 7.2 Hz); 6.85 (d, 2H, J=7.2 Hz); 6.98-7.01 (m, 2H); 7.20-7.24 (m, 3H); 7.47-7.53 (m, 2H); 7.86-7.88 (m, 2H); 11.01 (bs, 1H); MS for C31H32ClN5O4 m/z 574 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude residue was purified

Sources & evidence

ORD record
ord-42c096109025439692b703f33c4484b7
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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