1-Methylpiperazine → HCID 57688332, compound

HRID 731405Notes

Reaction equation

HRID 731405 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.Cl[C:18]1[S:22][C:21]([NH:23][C:24]([N:26]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:25])=[N:20][C:19]=1[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>C(Cl)Cl>[CH:27]1([N:26]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:24](=[O:25])[NH:23][C:21]2[S:22][C:18]([N:14]3[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]3)=[C:19]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[N:20]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 57883673HCID 57883673, compound

Product 1

HCID 57688332HCID 57688332, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (60 μl, 0.35 mmol) and N-methylpiperazine (33 μl, 0.298) were added to a solution of ethyl {5-chloro-2-[3,3-dicyclohexylureido]-thiazol-4-yl}-acetate (100 mg, 0.234 mmol) in methylene chloride (5 mL). The reaction mixture was stirred at room temperature for 48 h, filtered and evaporated to dryness in vacuo. The crude product was purified by HPLC to give ethyl {2-[3,3-dicyclohexylureido]-5-[4-methylpiperazin-1-yl]-thiazol-4-yl}-acetate. Yield: 13 mg (11%).

Workup

  1. filtrationfiltered
  2. customevaporated to dryness in vacuo
  3. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-bb9b866044364bb3b3255e1dadf1b303
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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