Ammonia → HCID 60104738, compound

HRID 1270250Notes

Reaction equation

HRID 1270250 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 CH2Cl2MeOH: 10/1 to give the title compound as a white solid (28 mg). 1H-MNR (CD3OD): δ 1.12 (d, 3H, J=6.8 Hz), 2.40 (m, 1H), 3.76 (dd, 1H, J1=12.8 Hz, J2=4.0 Hz), 3.94–4.04 (m, 2H), 4.33 (d, 1H, J=5.4 Hz), 6.13 (s, 1H), 8.11 (s, 1H), 8.16 (s, 1H).

Workup

  1. customThe solution was evaporated
  2. customthe residue purified on silica gel column with a solvent system of CH2Cl2MeOH

Sources & evidence

ORD record
ord-b472cd848aba48eda895b64a0dc95a0a
Source dataset
uspto-grants-2007_04
Patent number
US07202224B2

Reaction notes

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