Tetrahydrofuran → HCID 25065977, compound

HRID 2196606Notes

Reaction equation

HRID 2196606 reaction equation
[CH3:1][NH:2][CH3:3].O1CCCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O1CCCC1.[CH3:28][C:29]1[N:33]=[C:32]([NH:34][C:35]([C:37]2[C:42]([S:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][CH2:51][CH:52]=O)=[CH:46][CH:45]=3)=[CH:41][CH:40]=[C:39]([S:54][C:55]3[N:59]([CH3:60])[CH:58]=[N:57][N:56]=3)[N:38]=2)=[O:36])[S:31][N:30]=1>O.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:3])[CH2:52][CH2:51][O:50][C:47]1[CH:46]=[CH:45][C:44]([S:43][C:42]2[C:37]([C:35]([NH:34][C:32]3[S:31][N:30]=[C:29]([CH3:28])[N:33]=3)=[O:36])=[N:38][C:39]([S:54][C:55]3[N:59]([CH3:60])[CH:58]=[N:57][N:56]=3)=[CH:40][CH:41]=2)=[CH:49][CH:48]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 22320367Dimethylamine tetrahydrofuranHCID 86619610HCID 86619610, compound

Product 1

HCID 25065977HCID 25065977, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

0.25 ml of 2 M dimethylamine/tetrahydrofuran solution and 0.21 mg of sodium triacetoxyborohydride were added to a tetrahydrofuran solution of 166 mg of N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]-3-{[4-(2-oxoethoxy)phenyl]thio}pyridine-2-carboxamide obtained in the step 1, and stirred at room temperature for 30 minutes. Chloroform and saturated saline water were added to it, and extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the residue was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid). The solvent of the resulting fraction was evaporated away under reduced pressure to obtain 190 mg of the entitled compound as its trifluoroacetate. The obtained salt was neutralized, extracted with chloroform, and the organic layer was washed with saturated saline water. This was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the residue was purified through partitioning thin-layer chromatography (NH-PLC05 by Fuji Silicia Chemical, chloroform/methanol=95/5) to obtain 115 mg of the entitled compound as a yellow solid.

Workup

  1. customobtained in the step 1
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customthe residue was purified through reversed-phase middle-pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water/acetonitrile/0.1% trifluoroacetic acid)
  6. customThe solvent of the resulting fraction was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-b1d7ec3a697442de93f0cb54129b2501
Source dataset
uspto-grants-2012_12
Patent number
US08338460B2

Reaction notes

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