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

HRID 43395

Reaktionsgleichung

Reaktionsgleichung von HRID 43395
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[CH3:45][C@@H:46]1[CH2:51][NH:50][CH2:49][CH2:48][N:47]1[S:52]([C:55]1[CH:60]=[CH:59][C:58]([C:61]([F:64])([F:63])[F:62])=[CH:57][CH:56]=1)(=[O:54])=[O:53]>C(Cl)Cl.CN(C=O)C>[CH:8]([OH:10])=[O:9].[CH3:45][C@@H:46]1[CH2:51][N:50]([C:8]([C:5]2[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[O:10])[CH2:49][CH2:48][N:47]1[S:52]([C:55]1[CH:56]=[CH:57][C:58]([C:61]([F:64])([F:62])[F:63])=[CH:59][CH:60]=1)(=[O:54])=[O:53]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66649538(2R)-2-Methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride

Produkt 1

HCID 67028472(2R)-2-Methyl-4-[(6-methyl-3-pyridinyl)carbonyl]-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine formic acid salt

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-methyl-3-pyridinecarboxylic acid (47.7 mg, 0.348 mmol) in DCM (2.00 ml) was added HATU (132 mg, 0.348 mmol) and DIPEA (0.152 ml, 0.870 mmol) and the mixture stirred for 15 min before addition of (2R)-2-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride (Description 6) (100 mg, 0.290 mmol) in DMF (2 ml). The resultant mixture was stirred for 16 h at room temperature then the reaction mixture was concentrated and the residue taken up in DMSO and purified by MDAP. The collected fractions were concentrated in vacuo and triturated with isohexane giving the title compound (77.7 mg) as a white solid.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by MDAP
  3. concentrationThe collected fractions were concentrated in vacuo
  4. customtriturated with isohexane giving the title compound (77.7 mg) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-9f8dbd62de0a465e8744ee0cf50cc20a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536183B2

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