Methanol → HCID 88069648, compound

HRID 991561Notes

Reaction equation

HRID 991561 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[C:10]([C:11]([NH:13]/[C:14](=[C:20](\[C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:38])[C:30]3[C:35]([Cl:36])=[CH:34][N:33]=[CH:32][C:31]=3[Cl:37])=[CH:24][CH:23]=2)/[CH3:21])/[C:15]([O:17]CC)=[O:16])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1.CO>O1CCOCC1.O>[Cl:4][C:5]1[C:10]([C:11]([NH:13]/[C:14](=[C:20](\[C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:38])[C:30]3[C:31]([Cl:37])=[CH:32][N:33]=[CH:34][C:35]=3[Cl:36])=[CH:26][CH:27]=2)/[CH3:21])/[C:15]([OH:17])=[O:16])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 131723545HCID 131723545, compound

Product 1

HCID 88069648HCID 88069648, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide monohydrate (4.4 mg, 1.05 mml) was added to the compound of Example 16 (280 mg, 0.525 mmol) in a mixture of dioxane (10 ml) and water (10 ml). The mixture was heated at reflux for 2 h. The dioxane was removed in vacuo, the aqueous residue acidified with dilute HCl, the precipitate formed filtered off, washed with water and dried to give a brown solid. Trituration with hot methanol gave the title compound as a pale brown solid (94 mg). δH (DMSO-d6), 12.75 (1H,v br s,CO2H), 10.99 (1H, s, CONH), 9.75 (1H, s, CONH), 8.79 (2H, s, PyH), 8.44 (1H, dd, 14.8, 1.9 Hz, PyH), 7.68-7.64 (3H, m, ArH+PyH), 7.46 (1H, dd, J 7.5, 4.8 Hz, PyH), 7.38 (2H, d, J 8.6 Hz, ArH) and 2.33 (3H, s, Me); m/z (ESI, 70V) 505 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe dioxane was removed in vacuo
  4. customthe precipitate formed
  5. filtrationfiltered off
  6. washwashed with water
  7. customdried
  8. customto give a brown solid

Sources & evidence

ORD record
ord-7ff44dc3abec48b6896d3ff23aabb544
Source dataset
uspto-grants-2002_10
Patent number
US06465471B1

Reaction notes

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