Reaction equation
[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]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
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.
Workup
- concentrationthe reaction mixture was concentrated
- custompurified by MDAP
- concentrationThe collected fractions were concentrated in vacuo
- customtriturated with isohexane giving the title compound (77.7 mg) as a white solid
Sources & evidence
- ORD record
- ord-9f8dbd62de0a465e8744ee0cf50cc20a
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536183B2
Linked notes
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