Sodium Nitrite → HCID 86612908, compound

HRID 915883Notes

Reaction equation

HRID 915883 reaction equation
N[C:2]1[C:3]2[C:4]3[C:5](=[CH:13][N:14]([C@@H:16]4[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@@:17]4([CH3:25])[OH:18])[N:15]=2)[CH:6]=[CH:7][C:8]=3[C:9](=[O:12])[NH:10][N:11]=1.N([O-])=[O:27].[Na+]>C(O)(=O)C.CC[N+](CC)(CC)CC.[Br-]>[CH3:25][C@@:17]1([OH:18])[C@H:19]([OH:20])[C@@H:21]([CH2:23][OH:24])[O:22][C@H:16]1[N:14]1[CH2:13][C:5]2=[CH:6][CH:7]=[C:8]3[C:9](=[O:12])[NH:10][NH:11][C:2](=[O:27])[C:3](=[C:4]23)[NH:15]1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 86612909HCID 86612909, compound

Product 1

HCID 86612908HCID 86612908, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution 4-amino-2-(2-C-methyl-β-D-ribofuranosyl)-2,6-dihydro-7H-2,3,5,6-tetraazabenzo[cd]azulene-7-one 15.6 (35 mg, 0.1 mmol) in 50% aqueous acetic acid (5 mL) was added sodium nitrite (42 mg, 0.6 mmol) and the mixture stirred at room temperature for 4 hr. The mixture was neutralized with 1M TEAB buffer and purified by reversed phase ion-pairing HPLC on a Phenomenex Luna C18(2) 250×21 mm 10 μm column. 100 mM triethylammonium acetate (TEAA), pH 7 was used as the ion-pairing agent. A gradient of 20% to 55% MeOH over 40 min was applied. The target compound eluted at 26 min followed by two smaller peaks at 29 and 31 min. TEAA was removed by repeated lyophilzation to yield the target compound as a fluffy yellow material (28 mg, 80%).

Workup

  1. custompurified by reversed phase ion-pairing HPLC on a Phenomenex Luna C18(2) 250×21 mm 10 μm column
  2. waitA gradient of 20% to 55% MeOH over 40 min was applied
  3. washThe target compound eluted at 26 min
  4. customfollowed by two smaller peaks at 29 and 31 min
  5. customTEAA was removed

Sources & evidence

ORD record
ord-bde4b6bac418490bb38e70d3cf5f5a83
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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