Methanol → HCID 17853414, compound

HRID 584569Notes

Reaction equation

HRID 584569 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:29])[C:14]3[CH:19]=[C:18]([N:20]4[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH:22]=[N:21]4)[CH:17]=[CH:16][C:15]=3[Cl:28])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CO.[CH3:32][Si](C=[N+]=[N-])(C)C>O1CCOCC1>[C:1]12([CH2:11][NH:12][C:13](=[O:29])[C:14]3[CH:19]=[C:18]([N:20]4[C:25](=[O:26])[N:24]([CH3:32])[C:23](=[O:27])[CH:22]=[N:21]4)[CH:17]=[CH:16][C:15]=3[Cl:28])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 22341299HCID 22341299, compound

Product 1

HCID 17853414HCID 17853414, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of N-adamantan-1-ylmethyl-2-chloro-5-(3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-benzamide (66 mg, 0.159 mmol) in dioxane (1.5 ml) was added methanol (0.32 ml) followed by a 2.0 M solution of (trimethylsilyl)diazomethane (0.32 ml). After stirring for 18 hours at ambient temperature the mixture was concentrated under reduced pressure to give 67 mg of a light yellow amorphous solid. Mass Specrum (ES+) 429.6; (ES−) 427.6. Liquid chromatography retention time=2.8 min (using the LC/MS and method outlined for the examples in Table 1).

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac91ba3f01794f859df18fb20f44a217
Source dataset
uspto-grants-2005_08
Patent number
US06927219B2

Reaction notes

Loading…