Piperidine → HCID 68476315, compound
Reaction equation
ClC1C=CC([C@@H]2[C@@H]([C@@H](OC3C=CC(Cl)=C(Cl)C=3)C)CCN(C(C3CCN(C4C=CC(C#N)=CN=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.[Cl:71][C:72]1[CH:73]=[CH:74][C:75](O)=[N:76][CH:77]=1.ClC(OC(Cl)=O)C.CCN(C(C)C)C(C)C>CO>[Cl:71][C:72]1[CH:73]=[CH:74][C:75]([O:62][C@H:60]([C@H:57]2[CH2:58][CH2:59][NH:54][CH2:55][C@@H:56]2[C:63]2[CH:68]=[CH:67][C:66]([F:69])=[C:65]([F:70])[CH:64]=2)[CH3:61])=[N:76][CH:77]=1Participants
Reactant 6
HCID 8082Piperidine
HCID 81531Diisopropylethylamine
HCID 5213051-Chloroethyl chloroformate
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, compound
HCID 1785160645-chloropyridin-2-olProduct 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 5-Chloro-2-hydroxy-pyridine via Mitsunobu reaction and subsequently the benzyl group was cleaved by treatment with 1-chloroethyl-chloroformate, DIPEA and methanol to yield 5-Chloro-2-{(S)-1-[(3S,4S)-3-(3,4-difluoro-phenyl)-piperidin-4-yl]-ethoxy}-pyridine. 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): 566.4 [(M+H)+].
Sources & evidence
- ORD record
- ord-862ead0102704aefb48981f8285442d3
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324248B2
Reaction notes
Loading…