Water → 6'[(4-{[4-(Trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]-2,3'-bipyridine

HRID 41311Notes

Reaction equation

HRID 41311 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:27]=[N:28][C:29]([C:32](O)=[O:33])=[CH:30][CH:31]=1.C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:32]([C:29]3[N:28]=[CH:27][C:26]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=4)=[CH:31][CH:30]=3)=[O:33])[CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

8

Reactant 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57358853[2,3'-Bipyridine]-6'-carboxylic acid

Product 1

HCID 446120796'[(4-{[4-(Trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]-2,3'-bipyridineYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 1) (64.7 mg, 0.220 mmol) in DMF (3 ml) was added 2,3′-bipyridine-6′-carboxylic acid (Description 5) (44 mg, 0.220 mmol), HOBT.H2O (33.7 mg, 0.220 mmol), HBTU (83 mg, 0.220 mmol) and DIPEA (0.115 ml, 0.659 mmol) and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated under vacuum then DCM was added (5 ml) and washed with saturated NaHCO3 solution (5 ml). The product was concentrated under vacuum then dissolved in MeCN/DMSO 1:1 and purified by MDAP. The desired fractions were combined and evaporated under vacuum to give the title compound (83 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionDCM was added (5 ml)
  3. washwashed with saturated NaHCO3 solution (5 ml)
  4. concentrationThe product was concentrated under vacuum
  5. dissolutionthen dissolved in MeCN/DMSO 1:1
  6. custompurified by MDAP
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-7d8fa3a4639b47ca9d9ebdd81259f2fd
Source dataset
uspto-grants-2013_09
Patent number
US08530478B2

Reaction notes

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