Water → (2S)-2-Methyl-4-[(6-methyl-3-pyridinyl)carbonyl]-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid salt

HRID 43397

Reaktionsgleichung

Reaktionsgleichung von HRID 43397
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[N:63]=[CH:62][C:61]([C:64]([OH:66])=[O:65])=[CH:60][CH: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:61]2[CH:62]=[N:63][C:58]([CH3:57])=[CH:59][CH:60]=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]

Komponenten

8

Edukt 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1378606-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

Produkt 1

HCID 67028561(2S)-2-Methyl-4-[(6-methyl-3-pyridinyl)carbonyl]-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid saltAusbeute 142,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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 6-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, the organic layers were then concentrated to dryness and the crude material dissolved in DMSO and purified by MDAP giving the title compound (100.2 mg) as a colourless oil which solidified on standing.

Aufarbeitung

  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 were then concentrated to dryness
  5. dissolutionthe crude material dissolved in DMSO
  6. custompurified by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-f089adb1c31b4ba5b35f751b47bd6d2a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536183B2

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