Ammonia → 1-beta-d-Arabinofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine

HRID 1447009Notes

Reaction equation

HRID 1447009 reaction equation
[H][H].P([O-])([O-])([O-])=O.Cl[C:9]1[C:14]2[N:15]=[CH:16][NH:17][C:13]=2[CH:12]=[CH:11][N:10]=1.C([O:25][C@H:26]1[C@H:30]([O:31]CC2C=CC=CC=2)[C@@H:29]([CH2:39][O:40]CC2C=CC=CC=2)[O:28][C@@H:27]1Cl)C1C=CC=CC=1.[NH2:49]N.[Na].N>[Ni]>[C@@H:27]1([N:17]2[C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH2:49])[C:14]=3[N:15]=[CH:16]2)[O:28][C@H:29]([CH2:39][OH:40])[C@@H:30]([OH:31])[C@@H:26]1[OH:25]

Participants

9

Reactant 7

HCID 222AmmoniaHCID 1061PhosphateHCID 9321HydrazineHCID 5360545SodiumHCID 53733644-Chloro-1H-imidazo[4,5-c]pyridineHCID 10895454(2R,3R,4S,5R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-chlorotetrahydrofuranHCID 178418361HCID 178418361, compound2×

Product 1

HCID 127697241-beta-d-Arabinofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

An improved process for producing a compound of the formula ##STR7## wherein X is NH2, OH or SH; R is hydrogen or acyl containing 2 or 3 carbon atoms; and R1 is hydrogen, acyl containing 2 or 3 carbon atoms or phosphate which comprises β-D-arabinofuranosylating 4-chloro-1H-imidazo-[4,5-c]pyridine with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride; treating the resulting blocked nucleoside sequentially with hydrazine, Raney nickel and sodium in liquid ammonia to obtain 1-β-D-arabinofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine and acylating, phosphorylating, treating with sodium nitrate then phosphorus pentasulfide to obtain the desired compounds wherein the improvement comprises treating 4-chloro-1H-imidazo[4,5-c]pyridine with sodium hydride in a suitable solvent to form the anion having the formula ##STR8## and β-D-arabinofuranosylating said anion with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride.

Workup

  1. customAn improved process for producing a compound of the formula ##STR7## wherein X
  2. additiontreating the resulting

Sources & evidence

ORD record
ord-d410b21d64c947a89698e1a5f35b81dc
Source dataset
uspto-grants-1982_02
Patent number
US04315000

Reaction notes

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