Water → HCID 59161341, compound

HRID 43404

Reaction equation

HRID 43404 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.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.[CH3:56][C:57]1[CH:62]=[CH:61][N:60]=[CH:59][C:58]=1[C:63](O)=[O:64].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[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:63]([C:58]1[CH:59]=[N:60][CH:61]=[CH:62][C:57]=1[CH3:56])=[O:64]

Participants

9

Reactant 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2291634-Methylnicotinic acidHCID 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 59161341HCID 59161341, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (Description 2) (100 mg, 0.324 mmol) in DMF (5 ml) was added HOBT.H2O (49.7 mg, 0.324 mmol), HBTU (123 mg, 0.324 mmol), 4-methyl-3-pyridinecarboxylic acid (44.5 mg, 0.324 mmol) and DIPEA (0.170 ml, 0.973 mmol) and the reaction mixture was stirred for 1 h at room temperature. The reaction mixture was reduced in vacuo. The residue was dissolved in DCM (50 ml), transferred to a separating funnel and the solution was washed with aqueous NaHCO3 (5 ml), twice. The organic layer was dried with dried magnesium sulphate which was removed by filtration and the filtrate evaporated to dryness in vacuo. The residual oil was dissolved in 1:1 MeCN/DMSO (1.8 ml) and purified by MDAP in two batches. The fractions containing the desired product were combined and evaporated to dryness in vacuo. The residue was then dissolved in diethyl ether (50 ml) and transferred to a 100 ml round bottom flask and reduced to dryness in vacuo to yield the title compound (67 mg).

Workup

  1. customtransferred to a separating funnel
  2. washthe solution was washed with aqueous NaHCO3 (5 ml)
  3. dry with materialThe organic layer was dried with dried magnesium sulphate which
  4. customwas removed by filtration
  5. customthe filtrate evaporated to dryness in vacuo
  6. dissolutionThe residual oil was dissolved in 1:1 MeCN/DMSO (1.8 ml)
  7. custompurified by MDAP in two batches
  8. additionThe fractions containing the desired product
  9. customevaporated to dryness in vacuo
  10. dissolutionThe residue was then dissolved in diethyl ether (50 ml)
  11. customtransferred to a 100 ml round bottom flask

Sources & evidence

ORD record
ord-96a0a363d25c44d89643925c156f5a7e
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Linked notes

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