Sodium Hydroxide → HCID 118451601, compound

HRID 63704Notes

Reaction equation

HRID 63704 reaction equation
[OH-].[Na+].[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:44][C:45]([OH:48])([CH3:47])[CH3:46])[C:9]2[C:18]3[CH:17]=[CH:16][C:15]([C:19]([O:21]C)=[O:20])=[CH:14][C:13]=3[N:12]=[C:11]([NH:23][C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]=2[N:43]=1)[CH3:4]>C1COCC1.CO>[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:44][C:45]([OH:48])([CH3:47])[CH3:46])[C:9]2[C:18]3[CH:17]=[CH:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][C:13]=3[N:12]=[C:11]([NH:23][C:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]=2[N:43]=1)[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118451600HCID 118451600, compound

Product 1

HCID 118451601HCID 118451601, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide solution (1 N, 3.51 ml) was added to methyl 2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carboxylate (540 mg, 878 μmol) dissolved in THF (6.21 mL) and methanol (621 μL). The reaction mixture was stirred for 120 hours at room temperature and concentrated in vacuo. The residue was partitioned between ethyl acetate (30 mL) and cold 1M HCl solution (5 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). Organic layers were washed with water (20 mL) and brine (20 mL), combined, dried with MgSO4, and concentrated in vacuo to obtain the title compound (0.499 g, 94%) as white solid; LC-MS (UV peak area, ESI) 99%, 601.3 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate (30 mL) and cold 1M HCl solution (5 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. washOrganic layers were washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e67bb83c6c104b1aacfe5e81b9df41ea
Source dataset
uspto-grants-2016_09
Patent number
US09447097B2

Reaction notes

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