Hydrochloric Acid → HCID 59383097, compound

HRID 913157Notes

Reaction equation

HRID 913157 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14](C(OC(C)(C)C)=O)[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]3[CH2:27][O:26]C(C)(C)O3)=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC1C=C(C=CC=1OC)CN1CCC(NC2C=CC(CC)=CC=2)CC1)C.BrCCCOC1CCCCO1.C(=O)([O-])[O-].[K+].[K+].Cl.ClC1C=CC(CN2CCC(NC3C=CC(C#N)=CC=3)CC2)=CC=1OCC>CN(C=O)C.O1CCOCC1.C(O)C>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][CH2:27][OH:26])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 24854967HCID 24854967, compoundHCID 24854970HCID 24854970, compoundHCID 67400893HCID 67400893, compound

Product 1

HCID 59383097HCID 59383097, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared in analogy to the procedure described for rac-4-{tert-butoxycarbonyl-[5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-pyridin-2-yl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (intermediate B19/step 1) from 4-[tert-butoxycarbonyl-(5-hydroxy-pyridin-2-yl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (intermediate B18/step 5) by reaction with rac-2-(3-bromopropoxy)-tetrahydro-2H-pyran (commercially available) and potassium carbonate in DMF at rt, followed by BOC and THP cleavage with 4 M HCl in dioxane and ethanol at 70° C. in analogy to the synthesis of (5-methanesulfonyl-pyridin-2-yl)-piperidin-4-yl-amine (intermediate B16/step 2). MS (ISP): 252.1 [M+H]+.

Sources & evidence

ORD record
ord-58e9a2be87f444b4abfd8a52bf39e0a7
Source dataset
uspto-grants-2011_09
Patent number
US08026255B2

Reaction notes

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