Sodium Hydroxide → HCID 178481825, compound

HRID 1191223Notes

Reaction equation

HRID 1191223 reaction equation
[C:1]([C:5]1[C:6]([Cl:34])=[C:7]([C:11]2[NH:33][C:14]3[C:15]([O:29][CH2:30][CH:31]=[O:32])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C([OH:39])(C)(C)C.CC(=CC)C.O.Cl([O-])=O.[Na+].P([O-])(O)(O)=O.[Na+].[OH-].[Na+]>>[C:1]([C:5]1[C:6]([Cl:34])=[C:7]([C:11]2[NH:33][C:14]3[C:15]([O:29][CH2:30][C:31]([OH:39])=[O:32])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 14798Sodium HydroxideHCID 230840282-Methyl-2-butene t-butanol waterHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 178481823HCID 178481823, compound

Product 1

HCID 178481825HCID 178481825, compound

Procedure

To a mixture of [2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy]-acetaldehyde (30.0 mg, 0.0610 mmol, prepared as described in the previous step) in 5:5:2 tert-BuOH/2-methyl-2-butene/H2O (1.2 mL) was added sodium chlorite (11.6 mg, 0.128 mmol) followed by sodium dihydrogen phosphate (17.8 mg, 0.183 mmol). After stirring at room temperature for 16 h, the resulting mixture was treated with 1N NaOH (2 mL) and concentrated in vacuo. The resulting residue was treated with H2O (20 mL) and washed with EtOAc (2×10 mL). The aqueous phase was acidified to pH 5 by adding HOAc and then extracted with EtOAc (3×15 mL). The combined organic layers were washed with H2O (15 mL), brine (15 mL) and then dried with Na2SO4. Removal of the solvent in vacuo yielded [2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy]-acetic acid as a light yellow solid. 1H-NMR (400 MHz, CD3OD) δ: 7.13-8.04 (m, 5H), 5.10 (s, 2H), 4.06 (s, 3H), 1.43 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C23H21ClF3N5O3: 508.1 (M+H), Measured: 508.1.

Workup

  1. customprepared
  2. concentrationconcentrated in vacuo
  3. additionThe resulting residue was treated with H2O (20 mL)
  4. washwashed with EtOAc (2×10 mL)
  5. additionby adding HOAc
  6. extractionextracted with EtOAc (3×15 mL)
  7. washThe combined organic layers were washed with H2O (15 mL), brine (15 mL)
  8. dry with materialdried with Na2SO4
  9. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-a80bf62e5c13420b9ae5a3acb89d7859
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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