Lithium hydroxide, monohydrate → HCID 10082940, compound

HRID 1696919Notes

Reaction equation

HRID 1696919 reaction equation
COC1C=C(OC)C=CC=1C[N:12]1[C:21]2[C:16](=[C:17]([CH3:23])[CH:18]=[C:19]([Cl:22])[N:20]=2)[C:15](=[O:24])[C:14]([C:25]([O:27]CC)=[O:26])=[CH:13]1.O.[OH-].[Li+]>O1CCOCC1>[Cl:22][C:19]1[N:20]=[C:21]2[C:16]([C:15](=[O:24])[C:14]([C:25]([OH:27])=[O:26])=[CH:13][NH:12]2)=[C:17]([CH3:23])[CH:18]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 87333668HCID 87333668, compound

Product 1

HCID 10082940HCID 10082940, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Example 65D (0.200 g) in 1.4-dioxane (5 mL) was treated with lithium hydroxide monohydrate (0.100 g), stirred for 16 hours, and concentrated. The concentrate was dissolved in trifluoroacetic acid (8 mL), heated at 60° C. for 12 hours, and concentrated; and this concentrate was purified by reverse phase HPLC to afford the desired product. NMR (300 MHz, DMSO-d6) δ 14.95 (s, 1H), 13.79 (s, 1H), 8.72 (s, 1H), 7.57 (s, 1H), 2.89 (s, 3H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in trifluoroacetic acid (8 mL)
  3. concentrationconcentrated
  4. customand this concentrate was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c07e85739a01465da60c676a980ee42d
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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