HCID 118475082, compound → HCID 118451552, compound

HRID 522840Notes

Reaction equation

HRID 522840 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]([CH3:59])([CH3:58])[CH2:13][N:14]1[C:26]2[C:25]3[CH:24]=[CH:23][C:22](/[CH:27]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:21][C:20]=3[N:19]=[C:18]([NH:34][C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:17]=2[N:16]=[C:15]1[CH2:54][O:55][CH2:56][CH3:57])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]([CH3:58])([CH3:59])[CH2:13][N:14]1[C:26]2[C:25]3[CH:24]=[CH:23][C:22]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:21][C:20]=3[N:19]=[C:18]([NH:34][C:35]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:17]=2[N:16]=[C:15]1[CH2:54][O:55][CH2:56][CH3:57])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 118475082HCID 118475082, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 118451552HCID 118451552, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon 10% (100 mg, 940 μmol) in ethanol (10 mL) was added to a suspension of (E)-ethyl 3-(1-(2-(2-(tert-butoxycarbonylamino)ethoxy)-2-methylpropyl)-2-(ethoxymethyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinolin-7-yl)acrylate (280 mg, 351 μmol) in ethyl acetate (30 mL). The mixture was stirred for 6 h in a hydrogen atmosphere at room temperature, filtered and solvent was removed in vacuo. The residue was purified by flash chromatography (silica gel-NH2, 0% to 100% ethyl acetate in heptane) to give the title compound (0.163 g, 58%) as white solid; LC-MS (UV peak area, ESI) 74%, 800.5 (MH+).

Workup

  1. filtrationfiltered
  2. customsolvent was removed in vacuo
  3. customThe residue was purified by flash chromatography (silica gel-NH2, 0% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-9fced194a4504890a68794e295ef9fc5
Source dataset
uspto-grants-2016_05
Patent number
US09334268B2

Reaction notes

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