Ammonia → HCID 25001551, compound

HRID 1886865Notes

Reaction equation

HRID 1886865 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:21]#[N:22])[CH:9]=[C:10]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[N:6]2[N:5]=[CH:4][N:3]=1.N.[OH:24]O>C(O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:21]([NH2:22])=[O:24])[CH:9]=[C:10]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 25001248HCID 25001248, compound

Product 1

HCID 25001551HCID 25001551, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

to a solution of Compound 14 (12 mg) in ethanol (4.8 mL) was added 0.7 mL 28% aqueous ammonia and 0.18 mL 30% hydrogen peroxide. The mixture was stirred in a sealed vial at RT for 19 h. The solvent was removed in vacuo, and the crude product was purified on flash silica gel eluting with 10% MeOH in EtOAc to afford the product as pale yellow solid (9.1 mg). This material was recrystallised from EtOAc/MeOH to afford Compound 15 (6.5 mg) as a colourless solid: ESI-MS m/z 324 ([M+H]+); 1H NMR (500 MHz, d6-DMSO): δ 10.38 (d, J 3.1 Hz, 1H), 8.07 (br s, 1H), 8.04 (d, J 3.1 Hz, 1H), 7.91 (s, 1H), 7.52 (br s, 1H), 7.23 (s, 1H), 5.39 (s, 1H), 4.98 (d, J 7.4 Hz, 1H), 4.74 (s, 1H), 4.64 (t, J 5.8 Hz, 1H), 3.82-3.73 (m, 2H), 3.71-3.66 (m, 1H), 3.55 (dd, J 7.1 Hz, 8.3 Hz, 1H), 0.82 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified on flash silica gel eluting with 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-046c5f8a6c584e70a206db103f6636e6
Source dataset
uspto-grants-2013_08
Patent number
US08501699B2

Reaction notes

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