Potassium Cyanide → HCID 59619732, compound

HRID 445776Notes

Reaction equation

HRID 445776 reaction equation
C([O:5][C:6]([N:8]([CH2:42][CH3:43])[C:9]1[C:10]([CH2:37]OC(=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:7])(C)(C)C.[C-]#N.[K+]>CCO.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]6[CH2:37][O:7][C:6](=[O:5])[N:8]([CH2:42][CH3:43])[C:9]=6[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 9032Potassium CyanideHCID 59619676HCID 59619676, compound

Product 1

HCID 59619732HCID 59619732, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture 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 (stage 155.1.1, 0.107 mmol) and KCN (0.16 mmol) in EtOH (0.6 ml) was stirred for 17 h at 80° C. The RM was diluted with EtOAc and washed with water, with brine, dried over Na2SO4, filtered and evaporated. The residue The residue was absorbed on silica gel and purified by flash chromatography (CH2Cl2/MeOH 0% to 8%). The fractions containing product were evaporated together to give the title compound as an off-white solid. (HPLC: tR 2.42 min (Method A); M+H=470 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.00 (s, 1H), 8.35-8.32 (m, 1H), 8.17-8.13 (m, 1H), 8.11 (s, 1H), 8.04-8.00 (m, 1H), 7.62-7.59 (m, 1H), 7.49-7.47 (m, 1H), 5.40-5.31 (m, 2H), 4.04-3.85 (m, 2H), 3.87 (s, 3H), 3.59 (s, 3H), 1.97 (s, 3H), 1.24 (t, 3H))

Workup

  1. washwashed with water, with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue The residue was absorbed on silica gel
  6. custompurified by flash chromatography (CH2Cl2/MeOH 0% to 8%)
  7. additionThe fractions containing product
  8. customwere evaporated together

Sources & evidence

ORD record
ord-48581eeddfa248fd85b4b1be83396a9e
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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