Water → (2S)-2-methyl-1-(2-pyridinylcarbonyl)-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid salt

HRID 41308Notes

Reaction equation

HRID 41308 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3]1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([OH:29])=[O:28].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>[CH:27]([OH:29])=[O:28].[CH3:1][C@H:2]1[CH2:3][N:4]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)(=[O:9])=[O:10])[CH2:5][CH2:6][N:7]1[C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=1)=[O:28]

Participants

8

Reactant 6

HCID 962WaterHCID 1018Picolinic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59152086(S)-3-Methyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperazine

Product 1

HCID 44611963(2S)-2-methyl-1-(2-pyridinylcarbonyl)-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid saltYield 156.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 2) (80 mg, 0.259 mmol) in DMF (5 ml) was added 2-pyridinecarboxylic acid (31.9 mg, 0.259 mmol), HOBT.H2O (39.7 mg, 0.259 mmol), HBTU (98 mg, 0.259 mmol) and DIPEA (0.136 ml, 0.778 mmol) and the reaction mixture was stirred at room temperature overnight. DMF was evaporated in vacuo then 5 ml of DCM were added and washed with saturated NaHCO3 solution (5 ml), dried on a phase separation cartridge and evaporated in vacuo. The crude material was dissolved in MeCN/DMSO 1:1 and purified by MDAP. The desired fractions were collected and concentrated under vacuo giving the title compound (93 mg).

Workup

  1. customDMF was evaporated in vacuo
  2. addition5 ml of DCM were added
  3. washwashed with saturated NaHCO3 solution (5 ml)
  4. customdried on a phase separation cartridge
  5. customevaporated in vacuo
  6. dissolutionThe crude material was dissolved in MeCN/DMSO 1:1
  7. custompurified by MDAP
  8. customThe desired fractions were collected
  9. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-3fdf3a4d29164d49ac70013b48cdf0ee
Source dataset
uspto-grants-2013_09
Patent number
US08530478B2

Reaction notes

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