Sodium Hydroxide → HCID 87191929, compound

HRID 2089030Notes

Reaction equation

HRID 2089030 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17](S(C3C=CC=CC=3)(=O)=O)[CH:16]=2)[CH:3]=1.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=3)[NH:17][CH:16]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87192444HCID 87192444, compound

Product 1

HCID 87191929HCID 87191929, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of Example 178a (90.0 mg, 0.181 mmol) in dioxane (2.5 mL) was treated with 20% NaOH (0.12 mL). The reaction was heated at 50° C. for 4 hours. The solvent was evaporated and the residue was triturated with water. The solid was filtered and purified by reverse-phase HPLC as described in Example 56 to give the title compound (46.2 mg) as trifluoroacetic acid salts. 1H NMR (400 MHz, CD3OD) ppm 1.23-1.39 (m, 3H), 1.40-1.55 (m, 2H), 1.69 (m, 1H), 1.76-1.88 (m, 2H), 2.00-2.12 (m, 2H), 3.75 (m, 1H), 3.96 (s, 3H), 6.90 (d, J=1.22 Hz, 1H), 7.00 (d, J=1.53 Hz, 1H), 7.91 (d, J=2.44 Hz, 1H), 7.99 (s, 1H), 8.09 (d, J=2.75 Hz, 1H). MS (ESI+) m/z 357.5 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with water
  3. filtrationThe solid was filtered
  4. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-c33cd611cbf44e9e94d55e3c23c09572
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

Loading…