Diisopropylethylamine → 1-(3-Cyclohexyl-[1,2,4]thiadiazol-5-yl)-4-[2-(4-methoxy-phenyl)-ethyl]-piperazine

HRID 714404Notes

Reaction equation

HRID 714404 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[N:3]=1.Cl.Cl.[CH3:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C>CCO>[CH:7]1([C:4]2[N:3]=[C:2]([N:26]3[CH2:25][CH2:24][N:23]([CH2:22][CH2:21][C:20]4[CH:29]=[CH:30][C:17]([O:16][CH3:15])=[CH:18][CH:19]=4)[CH2:28][CH2:27]3)[S:6][N:5]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122357181-(4-Methoxyphenethyl)piperazine dihydrochlorideHCID 652672551423042-49-2

Product 1

HCID 712586661-(3-Cyclohexyl-[1,2,4]thiadiazol-5-yl)-4-[2-(4-methoxy-phenyl)-ethyl]-piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-chloro-3-cyclohexyl-1,2,4-thiadiazole (32.0 mg, 158 μmol), 1-(4-methoxyphenethyl)piperazine dihydrochloride (51.0 mg, 174 μmol) and DIPEA in EtOH was heated for 30 min at an oil bath temperature of 90° C. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions 13.7 mg (22%) of the title compound as light brown solid. MS (m/e): 387.3 (MH+).

Workup

  1. customThe mixture was subjected to purification by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and NEt3
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fractions 13.7 mg (22%) of the title compound as light brown solid

Sources & evidence

ORD record
ord-9909cef1c2ad425f8f2647c5361effa9
Source dataset
uspto-grants-2015_11
Patent number
US09187440B2

Reaction notes

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