Lithium Hydroxide → HCID 86582609, compound

HRID 718638Notes

Reaction equation

HRID 718638 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([NH:34][CH2:35][C:36]([O:38]CC)=[O:37])=[N:32][CH:33]=4)=[C:14](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[N:32][CH:33]=4)=[C:14](/[CH:16]=[CH:17]/[C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 117732503HCID 117732503, compound

Product 1

HCID 86582609HCID 86582609, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 45a (0.13 g, 0.24 mmol) in THF (3 mL) and water (2 mL) was added LiOH (30 mg, 1.25 mmol). The resulting solution was stirred at rt for 4 h, and concentrated under reduced pressure to remove volatile solvent. The pH of the resulting solution was adjusted to ˜4 with 1N HCl solution. The solids formed were collected by filtration. The crude solid was further purified by flash column chromatography on silica gel (1%-10% MeOH/DCM) to obtain the title compound 17 as a red solid. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 8.53 (d, J=8.7 Hz, 1H), 8.31-8.16 (m, 6H), 8.06-8.03 (m, 2H), 7.94-7.78 (m, 3H), 7.65 (t, J=7.5 Hz, 1H), 7.16 (d, J=9.3 Hz, 1H), 6.47 (d, J=5.7 Hz, 1H), 4.19-4.02 (m, 4H), 3.94-3.80 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H25N7O3: 508.2 (M+H). Found: 508.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove volatile solvent
  3. customThe solids formed
  4. filtrationwere collected by filtration
  5. customThe crude solid was further purified by flash column chromatography on silica gel (1%-10% MeOH/DCM)

Sources & evidence

ORD record
ord-9980203cc0214c55a27b4385dbf2939c
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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