Aminoethylpiperazine → HCID 69201356, compound

HRID 1392960Notes

Reaction equation

Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[NH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][O:9][C:7]([C:4]1[S:3][C:2]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][NH2:11])[CH2:15][CH2:16]2)=[N:6][CH:5]=1)=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 2-bromothiazole-5-carboxylate 1 (222 mg, 1.00 mmol) in acetonitrile (20 mL) were added N-(2-amino ethyl)piperazine 14d (155 mg, 1.20 mmol) and potassium carbonate (152 mg, 1.10 mmol) under a N2 atmosphere. The reaction mixture was heated to reflux at 80° C. for 10 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography using silica gel to give the compound 15d (176 mg, 65.2%).

Workup

temperatureThe reaction mixture was heated
filtrationThe reaction mixture was filtered through Celite
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-dfd3abd0ef8f4bac992b3a9be599ecb8
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345043B2

Reaction notes

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