Sodium Hydroxide → [4-(8-Bromo-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-acetic acid

HRID 445662Notes

Reaction equation

HRID 445662 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][N:5]1[CH:9]=[C:8]([N:10]2[C:22]3[C:21]4[CH:20]=[C:19]([Br:23])[CH:18]=[CH:17][C:16]=4[N:15]=[CH:14][C:13]=3[NH:12][C:11]2=[O:24])[C:7]([CH3:25])=[N:6]1.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>C(Cl)Cl>[Br:23][C:19]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[NH:12][C:11](=[O:24])[N:10]([C:8]4[C:7]([CH3:25])=[N:6][N:5]([CH2:4][C:3]([OH:26])=[O:2])[CH:9]=4)[C:22]=3[C:21]=2[CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16028TetrabutylammoniumHCID 59620049[4-(8-Bromo-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-acetic acid methyl ester

Product 1

HCID 59619756[4-(8-Bromo-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of [4-(8-bromo-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-acetic acid methyl ester (Stage 101.1.3, 3.22 g, 7.73 mmol) and tetrabutylammonium (250 mg, 0.773 mmol) in CH2Cl2 (150 ml) was added 1 M aqueous NaOH (80 ml). The reaction mixture was energetically stirred for 4 h 30 at rt. The organic layer was separted and the aqueous layer washed with CH2Cl2 (2×), adjusted to pH 4 with concentrated aqueous HCl and extracted with n-butanol (5×). The combined organic layers were washed with brine adjusted to pH 4 with HCl and evaporated to dryness. The residue was dry loaded on Isolute, washed with water/1-propanol 3% and eluted with acetonitrile/1-propanol 3% on reverse phase silica gel plug. To acetonitrile filtrate was added water and solution was concentrated. The formed precipitate was filtered, washed with water and dried to give the title compound as a yellow solid. (HPLC: tR 2.08 min (Method A); M+H=402, 404 Br-Pattern MS-ES)

Workup

  1. washthe aqueous layer washed with CH2Cl2 (2×)
  2. extractionextracted with n-butanol (5×)
  3. washThe combined organic layers were washed with brine
  4. customevaporated to dryness
  5. customThe residue was dry
  6. washwashed with water/1-propanol 3%
  7. washeluted with acetonitrile/1-propanol 3% on reverse phase silica gel plug
  8. additionTo acetonitrile filtrate was added water and solution
  9. concentrationwas concentrated
  10. filtrationThe formed precipitate was filtered
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-4fa34aaaec224499a9301175833dfad0
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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