Piperidine → HCID 68480531, compound
Reaction equation
ClC1C=CC([C@@H]2[C@@H]([C@@H](OC3C=CC(Cl)=C(Cl)C=3)C)CCN(C(C3CCN([C:33]4[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][N:34]=4)CC3)=O)C2)=CC=1.N1CCCCC1.C([N:54]1[CH2:59][CH2:58][C@H:57]([C@H:60]([OH:62])[CH3:61])[C@@H:56]([C:63]2[CH:68]=[CH:67][C:66]([F:69])=[C:65]([F:70])[CH:64]=2)[CH2:55]1)C1C=CC=CC=1.C(C1C=NC(O)=CC=1)#N.ClC(OC(Cl)=O)C.CCN(C(C)C)C(C)C>CO>[F:70][C:65]1[CH:64]=[C:63]([C@@H:56]2[C@@H:57]([C@@H:60]([O:62][C:33]3[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][N:34]=3)[CH3:61])[CH2:58][CH2:59][NH:54][CH2:55]2)[CH:68]=[CH:67][C:66]=1[F:69]Participants
Reactant 6
HCID 8082Piperidine
HCID 81531Diisopropylethylamine
HCID 5213051-Chloroethyl chloroformate
HCID 70621976-Hydroxynicotinonitrile
HCID 468708894-{(3S,4S)-3-(4-Chloro-phenyl)-4-[(S)-1-(3,4-dichloro-phenoxy)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carbonitrile
HCID 59438109HCID 59438109, compoundProduct 1
Reagents, catalysts & solvents 1
Procedure
In analogy to the procedure described for the synthesis of 4-{(3S,4S)-3-(4-Chloro-phenyl)-4-[(S)-1-(3,4-dichloro-phenoxy)-ethyl]-piperidine-1-carbonyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carbonitrile (example 49) the respective piperidine derivative was prepared from (R)-1-[(3S,4S)-1-Benzyl-3-(3,4-difluoro-phenyl)-piperidin-4-yl]-ethanol and 3-cyano-6-hydroxy-pyridine via Mitsunobu reaction and subsequently the benzyl group was cleaved by treatment with 1-chloroethyl-chloroformate, DIPEA and methanol to yield 6-{(S)-1-[(3S,4S)-3-(3,4-Difluoro-phenyl)-piperidin-4-yl]-ethoxy}-nicotinonitrile. Coupling with 5′-Cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (commercially available) yielded the title compound as off-white solid. MS (m/e): 557.3 [(M+H)+].
Sources & evidence
- ORD record
- ord-706edf6e6d9647b58d6e165a2b75b00f
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324248B2
Reaction notes
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