Ammonia → HCID 60104738, compound

HRID 1836229Notes

Reaction equation

HRID 1836229 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[N:12])=[CH:9][N:8]([C@@H:13]3[O:21][C@H:20]([CH2:22][O:23]C(=O)C4C=CC=CC=4)[C@@H:19]([CH3:32])[C@H:14]3[O:15]C(=O)C)[C:4]=2[N:5]=[CH:6][N:7]=1.N.[OH:34]O>>[NH2:1][C:2]1[C:3]2[C:10]([C:11]([NH2:12])=[O:34])=[CH:9][N:8]([C@@H:13]3[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([CH3:32])[C@H:14]3[OH:15])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 784Hydrogen PeroxideHCID 67142902HCID 67142902, compound

Product 1

HCID 60104738HCID 60104738, compound

Procedure

A mixture of the compound from Step B (51 mg, 0.12 mmol), ethanolic ammonia (5 mL, saturated at 0° C.), aqueous ammonia (5 mL, 30%) and aqueous hydrogen peroxide (1 mL, 35%) was stirred room temperature for 8 h. The solution was evaporated and the residue purified on silica gel column with a solvent system of CH2Cl2/MeOH: 10/1 to give the title compound as a white solid (28 mg).

Workup

  1. customThe solution was evaporated
  2. customthe residue purified on silica gel column with a solvent system of CH2Cl2/MeOH

Sources & evidence

ORD record
ord-473a10bc627040a39a8f0e2eec175019
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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