Pyridine → HCID 11635478, compound

HRID 2219068Notes

Reaction equation

HRID 2219068 reaction equation
[CH3:1][C@@:2]1([OH:23])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[C:12]([N+:20]([O-:22])=[O:21])=[CH:11]1.N1C=CC=CC=1.O(Cl)Cl.[O-:33][P:34]([O:37][P:38]([O-:41])([O-:40])=[O:39])(=[O:36])[O-:35].C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC.C([NH+](CCCC)CCCC)CCC.C[O:95][P:96](OC)(OC)=[O:97]>C1(C)C=CC=CC=1>[CH3:1][C@@:2]1([OH:23])[C@H:6]([OH:7])[C@@H:5]([CH2:8][O:9][P:96]([O:36][P:34]([O:37][P:38]([OH:41])([OH:40])=[O:39])([OH:35])=[O:33])([OH:97])=[O:95])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[C:12]([N+:20]([O-:22])=[O:21])=[CH:11]1

Participants

7

Reactant 5

HCID 1049PyridineHCID 10541Trimethyl PhosphateHCID 24646Chlorine monoxideHCID 21910867Tributyl ammonium pyrophosphateHCID 59770922HCID 59770922, compound

Product 1

HCID 11635478HCID 11635478, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 101 (57 mg, 1.5 mmol)) was dried by co-evaporation with dry pyridine (2×5 mL) and toluene (2×5 mL) and suspended in trimethylphosphate (5 mL). Phosphoro oxychloride (1.2 eq.) was added and reaction mixture kept for 2 h at 5° C. Tributylammonium pyrophosphate (1 mL of 2N solution in DMF) was added and the mixture was left overnight at 5° C. Reaction was quenched with Et3NHCO3 buffer and separated by RP-HPLC from 0 to 100% B, buffer A—water, buffer B—CH3CN. The major peak was collected, concentrated and repurified by RP-HPLC from 0 to 60% B. Buffers were as mentioned above. The major peak was collected and lyophilized;

Workup

  1. customreaction mixture
  2. waitthe mixture was left overnight at 5° C
  3. customReaction
  4. customwas quenched with Et3NHCO3 buffer and
  5. customseparated by RP-HPLC from 0 to 100% B, buffer A—water, buffer B—CH3CN
  6. customThe major peak was collected
  7. concentrationconcentrated
  8. customrepurified by RP-HPLC from 0 to 60% B
  9. customThe major peak was collected

Sources & evidence

ORD record
ord-cc3bb335844745b59a9f573402203b07
Source dataset
uspto-grants-2008_08
Patent number
US07414031B2

Reaction notes

Loading…