Chloride → HCID 49835672, compound

HRID 445683Notes

Reaction equation

HRID 445683 reaction equation
OC(C(F)(F)F)=O.[CH3:8][N:9]1[CH:13]=[C:12]([N:14]2[C:26]3[C:25]4[CH:24]=[C:23]([C:27]5[CH:28]=[N:29][C:30]([O:36][CH3:37])=[C:31]([CH:35]=5)[C:32](O)=[O:33])[CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][C:17]=3[N:16]([CH3:38])[C:15]2=[O:39])[C:11]([CH3:40])=[N:10]1.[Cl-].[CH3:42][NH2:43].C(O)C>ClCCl.CN(C=O)C>[CH3:8][N:9]1[CH:13]=[C:12]([N:14]2[C:26]3[C:25]4[CH:24]=[C:23]([C:27]5[CH:28]=[N:29][C:30]([O:36][CH3:37])=[C:31]([CH:35]=5)[C:32]([NH:43][CH3:42])=[O:33])[CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][C:17]=3[N:16]([CH3:38])[C:15]2=[O:39])[C:11]([CH3:40])=[N:10]1

Participants

7

Reactant 4

HCID 312ChlorideHCID 702EthanolHCID 6329MethylamineHCID 131730679HCID 131730679, compound

Product 1

HCID 49835672HCID 49835672, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled with an ice-bath suspension of 5-[1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl]-2-methoxy-nicotinic acid TFA salt (Example 124, 60 mg, 0.089 mmol) in dichloromethane (1.5 ml) containing DMF (0.005 ml) was added oxallyl chloride (0.038 ml, 0.449 mmol). The reaction mixture was stirred for 1 h at rt then cooled with an ice-bath and quenched with 8 M methylamine in ethanol (2.5 ml, 20 mmol). After 5 min stirring, the reaction mixture was evaporated to dryness and the residue purified by Prep.HPLC (H2O (0.1% TFA)/CH3CN 95:5 to 65:35). The fractions containing products were collected together, basified with NaHCO3, concentrated and the formed precipitate was filtered, washed with water and dried to give the title compound as white solid. (HPLC: tR 2.45 min (Method A); M+H=458 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.97 (s, 1H), 8.52-8.46 (m, 1H), 8.35-8.27 (m, 1H), 8.19-8.07 (m, 3H), 7.99-7.93 (m, 1H), 7.56-7.51 (m, 1H), 4.00 (s, 3H), 3.95 (s, 3H), 3.57 (s, 3H), 2.83 (d, 3H), 1.94 (s, 3H))

Workup

  1. temperatureTo a cooled with an ice-bath
  2. temperaturethen cooled with an ice-bath
  3. stirringAfter 5 min stirring
  4. customthe reaction mixture was evaporated to dryness
  5. customthe residue purified by Prep.HPLC (H2O (0.1% TFA)/CH3CN 95:5 to 65:35)
  6. additionThe fractions containing products
  7. customwere collected together
  8. concentrationconcentrated
  9. filtrationthe formed precipitate was filtered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-9c82732fb6814fb18d53a17770b75546
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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