8-[3'-(3-Aminopropoxy)biphenyl-4-ylmethylamino]-adenosine → HCID 178512989, compound

HRID 1713333Notes

Reaction equation

HRID 1713333 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]3[N:21]([C:31]4[N:32]=[CH:33][N:34]=[C:35]([NH2:38])[C:36]=4[N:37]=3)[C@@H:22]3[O:30][C@H:27]([CH2:28][OH:29])[C@@H:25]([OH:26])[C@H:23]3[OH:24])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.C(OC([NH:49][C:50](N1C=CC=N1)=[NH:51])=O)C1C=CC=CC=1>O1CCCC1.[Pd].CO>[NH:1]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH:19][C:20]3[N:21]([C:31]4[N:32]=[CH:33][N:34]=[C:35]([NH2:38])[C:36]=4[N:37]=3)[C@@H:22]3[O:30][C@H:27]([CH2:28][OH:29])[C@@H:25]([OH:26])[C@H:23]3[OH:24])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)[C:50]([NH2:51])=[NH:49]

Participants

6

Reactant 2

HCID 594604738-[3'-(3-Aminopropoxy)biphenyl-4-ylmethylamino]-adenosineHCID 137319688N-(Carbobenzoxy)-1H-pyrazole-1-carboxamidine

Product 1

HCID 178512989HCID 178512989, compoundYield 23.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

8-[3′-(3-Aminopropoxy)biphenyl-4-ylmethylamino]-adenosine (0.2 g) was suspended in tetrahydrofuran (2 mL), N-benzyloxycarbonyl-1H-pyrazole-1-carboxamidine (0.47 g) was added, and the resulting mixture was stirred at 60° C. for 24 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate/methanol=8/1-6/1). A mixture of the compound obtained and 10% palladium on carbon (43.8 wt % H2O, 0.05 g) in methanol (2 mL) was stirred at room temperature for 4 hours under a hydrogen atmosphere. The insoluble material was filtered out and the filtrate was concentrated under reduced pressure to give the title compound (0.05 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. customwas purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate/methanol=8/1-6/1)
  4. additionA mixture of the compound
  5. customobtained
  6. filtrationThe insoluble material was filtered out
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ba7e6f675c2748ae87111646fa9e88b1
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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