Lithium Hydroxide → HCID 49834899, compound

HRID 445707Notes

Reaction equation

HRID 445707 reaction equation
C(OC([N:8]([CH2:42][CH3:43])[C:9]1[C:10]([CH2:37][O:38]C(=O)C)=[N:11][CH:12]=[C:13]([C:15]2[CH:24]=[CH:23][C:22]3[N:21]=[CH:20][C:19]4[N:25]([CH3:36])[C:26](=[O:35])[N:27]([C:28]5[C:29]([CH3:34])=[N:30][N:31]([CH3:33])[CH:32]=5)[C:18]=4[C:17]=3[CH:16]=2)[CH:14]=1)=O)(C)(C)C.[Li+].[OH-]>O1CCOCC1.CCOC(C)=O>[CH3:33][N:31]1[CH:32]=[C:28]([N:27]2[C:18]3[C:17]4[CH:16]=[C:15]([C:13]5[CH:12]=[N:11][C:10]([CH2:37][OH:38])=[C:9]([NH:8][CH2:42][CH3:43])[CH:14]=5)[CH:24]=[CH:23][C:22]=4[N:21]=[CH:20][C:19]=3[N:25]([CH3:36])[C:26]2=[O:35])[C:29]([CH3:34])=[N:30]1

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 59619676HCID 59619676, compound

Product 1

HCID 49834899HCID 49834899, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of acetic acid 3-(tert-butoxycarbonyl-ethyl-amino)-5-[1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl]-pyridin-2-ylmethyl ester 155.1.1, 0.041 mmol) in dioxane (0.33 ml) was treated with 1 M aqueous LiOH (0.082 ml) for 1.5 h at rt then was added 1 M aqueous LiOH (0.082 ml) and the RM was stirred for 2 h at rt. The RM was diluted with EtOAc and washed with sat. aqueous NaHCO3, dried over Na2SO4, filtered and evaporated. The residue was taken in DMA and purified by preparative HPLC. The pure fraction was basified with NaHCO3, concentrated and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a film. (HPLC: tR 2.10 min (Method A); M+H=444 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.12-8.08 (m, 2H), 7.97-7.90 (m, 2H), 7.63-7.60 (m, 1H), 6.87 (s, 1H), 5.49 (t, 1H), 5.31 (t, 1H), 4.57 (d, 2H), 3.88 (s, 3H), 3.58 (s, 3H), 3.19 (qt, 2H), 1.96 (s, 3H), 1.25 (t, 3H))

Workup

  1. washwashed with sat. aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by preparative HPLC
  6. concentrationconcentrated
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customdried under vacuum

Sources & evidence

ORD record
ord-120882ff83574c1f941da98a5d36a45c
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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