Tetrahydrofuran → HCID 136337082, compound

HRID 1672811Notes

Reaction equation

HRID 1672811 reaction equation
O[N:2]=[C:3]([NH2:27])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:19][C@H:18]3[N:14]([CH2:15][CH2:16][CH2:17]3)[C:13]3[N:20]=[C:21]([S:24][CH3:25])[N:22]=[CH:23][C:12]=3[C:11]2=[O:26])[CH:5]=1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[S:29].C1C[O:43]CC1>C(OCC)(=O)C>[CH3:25][S:24][C:21]1[N:22]=[CH:23][C:12]2[C:11](=[O:26])[N:10]([C:6]3[CH:5]=[C:4]([C:3]4[NH:27][C:28](=[O:43])[S:29][N:2]=4)[CH:9]=[CH:8][CH:7]=3)[CH2:19][C@H:18]3[N:14]([CH2:15][CH2:16][CH2:17]3)[C:13]=2[N:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 802641,1'-ThiocarbonyldiimidazoleHCID 86643699(S)-N'-hydroxy-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzamidine

Product 1

HCID 136337082HCID 136337082, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(S)—N′-Hydroxy-3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)benzamidine (200 mg, 0.52 mmol) obtained in Step 1 of Example 75 was suspended in THF (3.0 mL), and the mixture was stirred at room temperature for 2 hours after adding 1,1′-thiocarbonyldiimidazole (155 mg, 0.78 mmol). After diluting the mixture with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration 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-thiadiazol-5(4H)-one (205 mg, 92%).

Workup

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe residue obtained upon concentration under reduced pressure
  4. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff87632008d24ae3bcfba019af957620
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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