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Water → 4-{[(3S)-3-methyl-4-(2-pyridinylcarbonyl)-1-piperazinyl]sulfonyl}benzonitrile

HRID 41316
Notes
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Reaction equation

HRID 41316 reaction equation
Cl.Cl.[CH3:3][C@H:4]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[O:11].CCN(C(C)C)C(C)C.[C:27]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)#[N:28].O>C(Cl)Cl>[CH3:3][C@@H:4]1[N:5]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])[CH2:6][CH2:7][N:8]([S:35]([C:32]2[CH:31]=[CH:30][C:29]([C:27]#[N:28])=[CH:34][CH:33]=2)(=[O:37])=[O:36])[CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 394974-Cyanobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67222743(2S)-2-methyl-1-(2-pyridinylcarbonyl)piperazine dihydrochloride

Product 1

HCID 446119604-{[(3S)-3-methyl-4-(2-pyridinylcarbonyl)-1-piperazinyl]sulfonyl}benzonitrileYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S)-2-methyl-1-(2-pyridinylcarbonyl)piperazine dihydrochloride (Description 16) (71 mg, 0.255 mmol) in DCM (3 ml) was added DIPEA (0.183 ml, 1.046 mmol) at room temperature and to it was slowly added 4-cyanobenzenesulfonyl chloride (56.6 mg, 0.281 mmol) and the resultant mixture then stirred for 3 h. 5 ml of water and 5 ml of DCM were added and the organic layer separated with a phase separation cartridge and then evaporated under vacuum. The crude material (120 mg) was purified via Biotage (12M silica column) using a gradient [i-hex/EtOAc] ([90/10] to [40/60]). The desired fractions were then collected and concentrated to dryness giving the title compound (48 mg) as a white solid.

Workup

  1. customthe organic layer separated with a phase separation cartridge
  2. customevaporated under vacuum
  3. customThe crude material (120 mg) was purified via Biotage (12M silica column)
  4. customThe desired fractions were then collected
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dc0910905023484a84df89cc4a67cb1f
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530478B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes