HCID 68974210, compound → HCID 136347852, compound

HRID 540901Notes

Reaction equation

HRID 540901 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-1eb17d510c9c4c94964bb3f880bd4113
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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