HCID 131730094, compound → HCID 131730095, compound

HRID 2191071Notes

Reaction equation

HRID 2191071 reaction equation
[NH4+:1].[NH4+].C([NH:11][C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[CH:21]1[O:25][CH:24]([CH:26]=[CH:27][P:28](=[O:31])([O-:30])[O-:29])[CH:23]([OH:32])[CH:22]1[F:33])(=O)C1C=CC=CC=1>[NH4+].[OH-]>[NH4+:11].[NH4+:1].[NH2:11][C:12]1[N:20]=[CH:19][N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[CH:21]1[O:25][CH:24]([CH:26]=[CH:27][P:28](=[O:29])([O-:30])[O-:31])[CH:23]([OH:32])[CH:22]1[F:33]

Participants

3

Reactant 1

HCID 131730094HCID 131730094, compound

Product 1

HCID 131730095HCID 131730095, compoundYield 195.9%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

Compound 56.3 (65 mg, 0.14 mmol) was dissolved in concentrated NH4OH (1.5 mL) and stirred for 24 h and then concentrated in vacuo. The residue was subjected to reverse phase HPLC eluting with 5-50% CH3CN-water gradient to give 56.4 (52 mg, 93% yield): white solid (bis-ammonium salt); 1H NMR (D2O, 300 MHz) 8.11 (s, 1H), 7.89 (s, 1H), 6.20 (m, 2H), 5.86 (app t, J=16.0 Hz, 1H), 4.84 (d, J=52.8 Hz, 1H), 4.16 (m, 2H); 31P NMR (D2O 121.4 MHz) 9.6; 19F NMR (D2O, 282 MHz) −195 (m, 1F); MS (ESI) m/z 346 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. washHPLC eluting with 5-50% CH3CN-water gradient

Sources & evidence

ORD record
ord-eab89ace7f2d46bfaba43092c4fac145
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

Loading…