Diisopropylethylamine → HCID 67028675, compound

HRID 2066124Notes

Reaction equation

HRID 2066124 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N: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:7]2[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=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]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6433732-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

Product 1

HCID 67028675HCID 67028675, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-3-pyridinecarboxylic acid (47.7 mg, 0.348 mmol) in DCM (2.000 ml) was added HATU (132 mg, 0.348 mmol) and DIPEA (0.152 ml, 0.870 mmol) and the mixture stirred for 15 minutes before addition of (2R)-2-methyl-l-{[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 then concentrated and the residue taken up in DMSO and purified by reverse phase MDAP. The collected fractions were concentrated in vacuo giving the the title compound (80.7 mg) as a white solid.

Workup

  1. concentrationthe reaction mixture was then concentrated
  2. custompurified by reverse phase MDAP
  3. concentrationThe collected fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-31cdc44fdc6b44a6bc881a79c9334336
Source dataset
uspto-grants-2012_10
Patent number
US08288388B2

Reaction notes

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