Methanol → HCID 10309984, compound

HRID 1767575Notes

Reaction equation

HRID 1767575 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([N:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[CH:22]=[N:21]2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])=[O:5].CO.[CH3:30][Si](C=[N+]=[N-])(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([N:20]2[C:25](=[O:26])[N:24]([CH3:30])[C:23](=[O:27])[CH:22]=[N:21]2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 10126799HCID 10126799, compound

Product 1

HCID 10309984HCID 10309984, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-chloro-N-[2-(2-chloro-phenyl)-ethyl]-5-(3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl)-benzamide (70 mg, 0.173 mmol) in dioxane (1.5 ml) was added methanol (0.36 ml) followed by a 2.0 M solution of (trimethylsilyl)diazomethane (0.35 ml). After stirring for 16 hours at ambient temperature the mixture was concentrated under reduced pressure to give 75 mg of a white amorphous solid. Purification by silica gel chromatography eluting with 2:1 hexaned/ethyl acetate provided 39 mg of the title compound as a white amorphous solid. Melting Point 157–161° C.;

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-9056bfe8390c4d94bfdb98ddc59e7137
Source dataset
uspto-grants-2007_06
Patent number
US07235549B2

Reaction notes

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