HCID 68974210, compound → HCID 136347852, compound

HRID 2203576Notes

Reaction equation

HRID 2203576 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:20]([CH2:34][O:35][CH2:36][CH3:37])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>[Pd].C(O)C.CO>[CH2:36]([O:35][CH2:34][C:20]1[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:13]2[C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:19]=1)[CH3:37]

Participants

4

Reactant 1

HCID 68974210HCID 68974210, compound

Product 1

HCID 136347852HCID 136347852, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

A mixture of tert-butyl 4-[7-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butylcarbamate (15 g, 29.7 mmol) and 10% palladium on carbon (4.5 g, wetted with ethanol) in 1:1 ethanol/methanol (400 mL) was hydrogenated using a Parr apparatus at 28 psi (1.9×105 Pa) for 16 hours. The mixture was filtered through CELITE filter agent, which was subsequently washed with methanol. The filtrate was concentrated under reduced pressure to afforded 10.8 g of tert-butyl 4-[2-(ethoxymethyl)-7-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl]butylcarbamate as a green-yellow solid.

Workup

  1. customfor 16 hours
  2. filtrationThe mixture was filtered through CELITE
  3. filtrationfilter agent, which
  4. washwas subsequently washed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c18f47ce0b924e4a8dbece58a470b5f9
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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