Triethylamine → Pyrazine-2-carboxylic acid {4-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-amide

HRID 2211894Notes

Reaction equation

HRID 2211894 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[N:2]1.C(N(CC)CC)C.[N:32]1[CH:37]=[CH:36][N:35]=[CH:34][C:33]=1[C:38](Cl)=[O:39]>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:38]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][N:32]=4)=[O:39])=[CH:22][CH:23]=3)[CH2:14][CH2:15]2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 88279Pyrazinecarbonyl chlorideHCID 219631764-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine

Product 1

HCID 86594328Pyrazine-2-carboxylic acid {4-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4-[2-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-phenylamine was diluted to 0.40 M with anhydrous dichloromethane, then delivered to an 8 mL vial via pipette (0.2 mmol). To the amine solution was added base (0.4 M triethylamine in dichloromethane, 0.20 mmol). Pyrazine-2-carbonyl chloride was diluted to 0.40 M with dichloromethane, and added at rt (0.2 mmol). The reaction was shaken overnight at rt, then evaluated by MS. The reaction was concentrated using an HT-12 GeneVac, then purified by HPLC (30×100 mm ODS-A C(18) 5u column). Pyrazine-2-carboxylic acid {4-[2-(4-1,2-benzisothiazol-3-yl-piperazin-1-yl)-ethyl]-phenyl}-amide was isolated in 88% purity @ 254 nm, LCMS (APCI): 445 [M+H]+.

Workup

  1. additionadded at rt (0.2 mmol)
  2. concentrationThe reaction was concentrated
  3. custompurified by HPLC (30×100 mm ODS-A C(18) 5u column)

Sources & evidence

ORD record
ord-3395d89d78ea4691b81f42a4853b0753
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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