Water → HCID 67028571, compound

HRID 43398Notes

Reaction equation

HRID 43398 reaction equation
Cl.[CH3:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10].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.[CH3:57][C:58]1[C:63]([C:64]([OH:66])=[O:65])=[CH:62][CH:61]=[CH:60][N:59]=1.CCN(C(C)C)C(C)C>C1COCC1>[CH:64]([OH:66])=[O:65].[CH3:2][C@H:3]1[CH2:8][N:7]([C:64]([C:63]2[C:58]([CH3:57])=[N:59][CH:60]=[CH:61][CH:62]=2)=[O:65])[CH2:6][CH2:5][N:4]1[S:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=1)(=[O:11])=[O:10]

Participants

8

Reactant 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6433732-Methylnicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66649356(2S)-2-Methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride

Product 1

HCID 67028571HCID 67028571, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-2-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride (Description 8) (100 mg, 0.270 mmol) in THF (5 ml) was added HOBT.H2O (41.3 mg, 0.270 mmol), HBTU (102 mg, 0.270 mmol) and 2-methyl-3-pyridinecarboxylic acid (40.7 mg, 0.297 mmol). The mixture was stirred for 5 min before addition of DIPEA (0.118 ml, 0.674 mmol) and the resultant solution stirred at room temperature for 16 h. The mixture was then concentrated and the residue partitioned between DCM (10 ml) and water (10 ml), the layers were separated using a hydrophobic frit and the organic layers concentrated to dryness and the crude dissolved in DMSO and purified by MDAP giving the title compound (61.2 mg) as a white solid.

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue partitioned between DCM (10 ml) and water (10 ml)
  3. customthe layers were separated
  4. concentrationthe organic layers concentrated to dryness
  5. dissolutionthe crude dissolved in DMSO
  6. custompurified by MDAP

Sources & evidence

ORD record
ord-471cad981a75419a99bd2f328d447b30
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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