Diisopropylethylamine → HCID 53353526, compound

HRID 451435Notes

Reaction equation

HRID 451435 reaction equation
Cl.[CH2:2]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:23][C:24]1[N:28]=[C:27](Cl)[S:26][N:25]=1.C(N(CC)C(C)C)(C)C>O1CCCC1.O>[CH2:2]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:27]3[S:26][N:25]=[C:24]([Cl:23])[N:28]=3)[CH2:19][CH2:18]2)[N:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725055Dichloro-1,2,4-thiadiazoleHCID 67344140HCID 67344140, compound

Product 1

HCID 53353526HCID 53353526, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-benzyl-6-methyl-pyrimidin-2-yl)-piperidin-4-yl-amine hydrochloride (159 mg, 0.5 mmol), 3,5-dichloro-[1,2,4]thiadiazol (39 mg, 0.25 mmol) and N,N-diisopropylethylamine (85 L, 0.5 mmol) in tetrahydrofurane (2 mL) was heated to 95° C. 4 hours under nitrogen. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using Et2O as eluent. The title compound was obtained as a colorless oil (52 mg, 52%).

Workup

  1. custom4 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-28760e8c971047d4b42f8539e7f09ff5
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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