Methanol → HCID 86591392, compound

HRID 346988Notes

Reaction equation

HRID 346988 reaction equation
[CH:1]1N=CN(C(N2C=NC=C2)=O)C=1.O.Cl.[Cl:15][C:16]1[CH:17]=[C:18]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:32]([OH:48])([C:42]4[N:46]([CH3:47])[CH:45]=[N:44][CH:43]=4)[C:33]4[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=4)[CH:30]=3)[NH:25][C:24](=[O:49])[CH:23]=2)[CH:19]=[CH:20][CH:21]=1.N12CCN(CC1)CC2.CO>C1COCC1.O>[Cl:15][C:16]1[CH:17]=[C:18]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:32]([OH:48])([C:42]4[N:46]([CH3:47])[CH:45]=[N:44][CH:43]=4)[C:33]4[CH:34]=[CH:35][C:36]([C:37]([O:39][CH3:1])=[O:38])=[CH:40][CH:41]=4)[CH:30]=3)[NH:25][C:24](=[O:49])[CH:23]=2)[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 9237DabcoHCID 682631,1'-CarbonyldiimidazoleHCID 69521716HCID 69521716, compound

Product 1

HCID 86591392HCID 86591392, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

CDI (0.00925 mol) was added to a mixture of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzoic acid monohydrochloride monohydrate (described in Example B3) (0.00185 mol) in THF (10 ml). The mixture was stirred at 40° C. for 1 hour.1,4 diazabicyclo[2,2,2]octane (0.00185 mol) and methanol (5 ml) were added. The mixture was stirred at 40° C. for 18 hours, poured out into H2O and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 0.44 g (48%) of (±-methyl 4-[[4-(3-chlorophenyl)-1,2-dihydro-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzoate, mp. 255° C.

Workup

  1. stirringThe mixture was stirred at 40° C. for 18 hours
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was crystallized from 2-propanone
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-de395b684f4e451da7c16ff452d3c5f9
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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