Lithium hydroxide, monohydrate → 17-[2-(3-Isopropylpyrazol-1-yl)-7-methoxy-8-methylquinazolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid

HRID 1443496Notes

Reaction equation

HRID 1443496 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]12[CH2:26][CH:25]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20][CH2:19][N:18]([CH3:27])[C:17](=[O:28])[CH:16]1[CH:12]([CH2:13][CH:14]([O:29][C:30]3[C:39]4[C:34](=[C:35]([CH3:42])[C:36]([O:40][CH3:41])=[CH:37][CH:38]=4)[N:33]=[C:32]([N:43]4[CH:47]=[CH:46][C:45]([CH:48]([CH3:50])[CH3:49])=[N:44]4)[N:31]=3)[CH2:15]1)[C:11](=[O:51])[NH:10]2)=[O:8])C>O.C1COCC1>[CH:48]([C:45]1[CH:46]=[CH:47][N:43]([C:32]2[N:31]=[C:30]([O:29][CH:14]3[CH2:13][CH:12]4[CH:16]([C:17](=[O:28])[N:18]([CH3:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH:25]5[C:9]([C:7]([OH:8])=[O:6])([NH:10][C:11]4=[O:51])[CH2:26]5)[CH2:15]3)[C:39]3[C:34](=[C:35]([CH3:42])[C:36]([O:40][CH3:41])=[CH:37][CH:38]=3)[N:33]=2)[N:44]=1)([CH3:50])[CH3:49]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68688284HCID 68688284, compound

Product 1

HCID 6868954017-[2-(3-Isopropylpyrazol-1-yl)-7-methoxy-8-methylquinazolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide hydrate (796 mg, 18.6 mmol) in water (10 mL) was added to a stirred solution of the ester (145) (346 mg, 0.526 mmol) in THF (30 mL). After 5 days at room temperature, the reaction mixture was concentrated under vacuum. The pH was adjusted to 4 with 1N HCl and the resulting solution was successively extracted with AcOEt, washed with brine, dried (Na2SO4) and evaporated.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. extractionthe resulting solution was successively extracted with AcOEt
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-456e7c9b35144961b7548638a99cd33f
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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