Methanol → HCID 59619792, compound

HRID 445765Notes

Reaction equation

HRID 445765 reaction equation
C[O:2][C:3](=O)[C:4]([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]2[CH:22]=[CH:21][C:20]3[N:19]=[CH:18][C:17]4[N:23]([CH3:34])[C:24](=[O:33])[N:25]([C:26]5[C:27]([CH3:32])=[N:28][N:29]([CH3:31])[CH:30]=5)[C:16]=4[C:15]=3[CH:14]=2)[CH:12]=1)([CH3:6])[CH3:5].CO.[BH4-].[Na+]>C1COCC1>[CH3:31][N:29]1[CH:30]=[C:26]([N:25]2[C:16]3[C:15]4[CH:14]=[C:13]([C:11]5[CH:10]=[N:9][CH:8]=[C:7]([C:4]([CH3:6])([CH3:5])[CH2:3][OH:2])[CH:12]=5)[CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][C:17]=3[N:23]([CH3:34])[C:24]2=[O:33])[C:27]([CH3:32])=[N:28]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 59620097HCID 59620097, compound

Product 1

HCID 59619792HCID 59619792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{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-3-yl}-2-methyl-propionic acid methyl ester (Stage 229.1.1, 0.134 mmol) in THF (1.2 ml) were added MeOH (0.009 ml) and NaBH4 (0.185 mmol) four times during the course of the heating at 40° C. for 39 h. After that, the RM was quenched with saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was taken in DMF and purified by preparative HPLC. The fractions containing product were basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a white foam. (HPLC: tR 2.06 min (Method A); M+H=442 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.99 (s, 1H), 8.62-8.58 (m, 2H), 8.15-8.11 (m, 2H), 8.01-7.96 (m, 1H), 7.74-7.71 (m, 1H), 7.62-7.59 (m, 1H), 4.79 (t, 1H), 3.88 (s, 3H), 3.58 (s, 3H), 3.50 (d, 2H), 1.96 (s, 3H), 1.30 (s, 6H))

Workup

  1. customAfter that, the RM was quenched with saturated aqueous NaHCO3
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by preparative HPLC
  8. additionThe fractions containing product
  9. concentrationconcentrated
  10. extractionextracted with dichloromethane (2×)
  11. washThe combined organic layers were washed with brine
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. customevaporated
  15. customdried under vacuum

Sources & evidence

ORD record
ord-6d350974c0584a1d8eeb8a01815f1250
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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