Diisopropylethylamine → (S)-1-Cyano-cyclopropanecarboxylic acid (1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-amide
Reaction equation
[C:1]([C:3]1([C:6]([OH:8])=O)[CH2:5][CH2:4]1)#[N:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH2:43]([O:45][C:46]1[CH:51]=[CH:50][C:49]([CH:52]2[CH2:57][CH2:56][N:55]([C:58]3[CH:63]=[CH:62][C:61]([C@@H:64]([NH2:66])[CH3:65])=[CH:60][CH:59]=3)[CH2:54][CH2:53]2)=[CH:48][CH:47]=1)[CH3:44]>CN(C=O)C>[CH2:43]([O:45][C:46]1[CH:47]=[CH:48][C:49]([CH:52]2[CH2:53][CH2:54][N:55]([C:58]3[CH:59]=[CH:60][C:61]([C@@H:64]([NH:66][C:6]([C:3]4([C:1]#[N:2])[CH2:5][CH2:4]4)=[O:8])[CH3:65])=[CH:62][CH:63]=3)[CH2:56][CH2:57]2)=[CH:50][CH:51]=1)[CH3:44]Participants
6
Reactant 4
HCID 81531Diisopropylethylamine
HCID 27332591-Cyanocyclopropanecarboxylic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 86688559(S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochlorideProduct 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 14 mg (0.13 mmol) 1-cyano-cyclopropanecarboxylic acid in 1 mL DMF are added 52 μL (0.30 mmol) DIPEA and 49 mg (0.13 mmol) HATU. The mixture is stirred for 10 min at rt. Subsequently a mixture of 36 mg (0.10 mmol) (S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride (XII.1) in 1 mL DMF is added and stirring is continued for 6 h at rt. The crude mixture is directly purified by HPLC (Sunfire, narrow gradients, water (+0.1% TFA)/methanol) to yield the desired product.
Workup
- additionis added
- stirringstirring
- waitis continued for 6 h at rt
- customThe crude mixture is directly purified by HPLC (Sunfire, narrow gradients, water (+0.1% TFA)/methanol)
Sources & evidence
- ORD record
- ord-e5a3d201eb514b329bf0366ea9346ac5
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765959B2
Reaction notes
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