Hydrochloric Acid → HCID 10294880, compound

HRID 1295133Notes

Reaction equation

HRID 1295133 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][NH:26][C:27]3[NH:28][CH2:29][CH2:30][N:31]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>CO.O>[NH:28]1[CH2:29][CH2:30][N:31]=[C:27]1[NH:26][O:25][CH2:24][CH2:23][O:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[N:13]([CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:5][C:4]([OH:32])=[O:3])[CH:14]=[CH:15]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86600673HCID 86600673, compound

Product 1

HCID 10294880HCID 10294880, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

3-(5-{2-[N-(4,5-dihydro-1H-imidazol-2-yl)-aminooxy]-ethoxy}-indol-1-yl)-3-phenyl-propionic acid ethyl ester (0.24 g, 0.55 mmol) was dissolved in 70% methanol/water (4 mL). Lithium hydroxide monohydratate (0.70 g, 4.67 mmol) was added and the reaction was stirred for 16 h at room temperature under an argon atmosphere. The solution was neutralized with 1.0 N HCl (4.67 mL) and the solvent was evaporated under vacuum. The crude mixture was purified via column chromatography with silica gel, eluting with 10% methanol/dichloromethane to afford the title compound (74% yield). 1H NMR (DMSO-d6) δ 7.68 (d, 1H, J=3.2 Hz), 7.42 (d, 1H, J=9.0 Hz), 7.20–7.34 (m, 5H), 7.05 (d, 1H, J=2.5 Hz), 6.75 (dd, 1H, J=2.5, 9.0 Hz), 6.40 (d, 1H, J=3.0 Hz), 5.96 (m, 1H), 4.16 (m, 4H), 3.59 (br s, 4H), 3.36 (m, 2H). Mass Spectrum (LCMS, ESI) calculate for C22H25N4O4 409.2 (M+H); found 409.2.

Workup

  1. customthe solvent was evaporated under vacuum
  2. customThe crude mixture was purified via column chromatography with silica gel
  3. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-99f9004068f94599850537906144f6b0
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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