Propylamine → HCID 136150022, compound

HRID 2263417Notes

Reaction equation

HRID 2263417 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[C:27]1[NH:31][C:30](=[O:32])[O:29][N:28]=1)[O:5][CH2:6][C:7]1[S:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH:22]=O.[CH2:33]([NH2:36])[CH2:34][CH3:35].C(N(CC)CC)C.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH2:22][NH:36][CH2:33][CH2:34][CH3:35])[CH:24]=[CH:25][C:26]=1[C:27]1[NH:31][C:30](=[O:32])[O:29][N:28]=1

Participants

6

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 136149935HCID 136149935, compound

Product 1

HCID 136150022HCID 136150022, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg 5-[3-Methyl-4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazole-4-carbaldehyde and 12.8 mg propylamine were suspended in 3 ml methanol. 30.0 μl triethylamine were added upon the reaction mixture became a clear solution. 400 mg molecular sieves four angstrom were added and the reaction mixture stirred at room temperature for two hours. Then 8.2 mg sodium borohydride were added and the reaction mixture stirred at room temperature for thirty minutes. The reaction mixture was filtered through a celite pad. The filtrate was evaporated in vacuo and then evaporated in vacuo. The residue was purified by RP-HPLC to obtain 45.7 mg 3-{2-methyl-4-[4-propylaminomethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one as its trifluoroacetate salt.

Workup

  1. addition400 mg molecular sieves four angstrom were added
  2. stirringthe reaction mixture stirred at room temperature for thirty minutes
  3. filtrationThe reaction mixture was filtered through a celite pad
  4. customThe filtrate was evaporated in vacuo
  5. customevaporated in vacuo
  6. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-a42296ba7d45472ea23a2de8a3c99a7b
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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