Water → HCID 11112927, compound

HRID 353136Notes

Reaction equation

HRID 353136 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][N:18]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([O:32]CC)=[O:31])=[CH:26][CH:25]=2)=[O:22])[CH2:17][CH2:16]1.O.[OH-].[Li+].O>O1CCOCC1>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:21]([N:18]2[CH2:19][CH2:20][N:15]([C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)[CH2:16][CH2:17]2)=[O:22])=[CH:25][CH:26]=1)([OH:32])=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrate2×HCID 11081103HCID 11081103, compound

Product 1

HCID 11112927HCID 11112927, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 390 mg (0.84 mmol) of 4-(6,7-dimethoxy-4-quinazolinyl)-N-(4-ethoxycarbonylphenyl)-1-piperazinecarboxamide obtained in Example 89 in 10 ml of 1,4-dioxane were added 70.4 mg (1.68 mmol) of lithium hydroxide monohydrate and 1 ml of water, followed by stirring at room temperature for 4.5 hours. To the resulting mixture was further added 70.4 mg (1.68 mmol) of lithium hydroxide monohydrate, followed by overnight stirring at room temperature. After the solvent was evaporated, water was added to the residue, and the resulting mixture was adjusted to pH 4 with 4 N hydrochloric acid. The precipitated crystals were collected by filtration, washed with water, and dried, followed by purification by silica gel column chromatography to give the desired compound as colorless crystals.

Workup

  1. waitfollowed by overnight
  2. stirringstirring at room temperature
  3. customAfter the solvent was evaporated
  4. additionwater was added to the residue
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water
  7. customdried
  8. customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record
ord-348853720e1f474ebdd7cc53b39c859d
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Reaction notes

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