Ammonia methanol → HCID 67350635, compound

HRID 1672801Notes

Reaction equation

HRID 1672801 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[N:27]=[C:26]([C:28]([O:30]C)=O)[O:25][N:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:32]=1.[NH3:33].CO>CO>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[N:27]=[C:26]([C:28]([NH2:33])=[O:30])[O:25][N:24]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:32]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 67349186HCID 67349186, compound

Product 1

HCID 67350635HCID 67350635, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (S)-3-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazole-5-carboxylate (320 mg, 0.71 mmol) obtained in Step 1 of Example 80 was dissolved in methanol (3.0 mL), and the mixture was stirred at room temperature for 3 hours after adding a 2.0 mol/L ammonia/methanol solution (3.50 mL, 7.07 mmol). The residue obtained by concentrating the mixture under reduced pressure was then purified by silica gel column chromatography to give (S)-3-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,2,4-oxadiazole-5-carboxamide (300 mg, 96%).

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the mixture under reduced pressure
  3. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-12174f019dbc445eaab8401453b7f310
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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