Ammonia → HCID 135453913, compound

HRID 402320Notes

Reaction equation

HRID 402320 reaction equation
[CH:1]1[N:5]([C@@H:6]2[O:10][C@H:9]([CH2:11][O:12]P(O)(O)=O)[C@@H:8]([OH:17])[C@H:7]2[OH:18])[C:4]([NH2:19])=[C:3]([C:20]([NH2:22])=[O:21])[N:2]=1.[N:23]([O-])=O.[Na+].N>C(O)C>[C@@H:6]1([N:5]2[C:4]3[N:19]=[N:23][NH:22][C:20](=[O:21])[C:3]=3[N:2]=[CH:1]2)[O:10][C@H:9]([CH2:11][OH:12])[C@@H:8]([OH:17])[C@H:7]1[OH:18]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 65110AICAR monophosphateHCID 23668193Sodium Nitrite

Product 1

HCID 135453913HCID 135453913, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The AICAR [for preparation see Synthesis, 2003. No 17, 2639] (1 g, 3.87 mmol) was added to a solution of chlorhydrique acid 6N (25 mL) at −30° C. A solution of sodium nitrite 3M (4 ml, 11.62 mmol) was added and the mixture was stirred at −30° for 2 hours. A pre-cooled (−30° C.) solution of ethanol (25 mL) was added. A solution of ammonia (28%) was added at −20° C. to pH=7. The reaction mixture was evaporated to dryness. The crude product was purified on silica gel reverse-phase (C18) using water as eluant to give the title compound (0.81 gr) as a white powder.

Workup

  1. customSynthesis, 2003
  2. additionNo 17, 2639] (1 g, 3.87 mmol) was added to a solution of chlorhydrique acid 6N (25 mL) at −30° C
  3. additionwas added
  4. customThe reaction mixture was evaporated to dryness
  5. customThe crude product was purified on silica gel reverse-phase (C18)

Sources & evidence

ORD record
ord-dc717a454026474db432cb9ecbcf1623
Source dataset
uspto-grants-2014_06
Patent number
US08742101B2

Reaction notes

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