Hydrochloric Acid → HCID 87254190, compound

HRID 337697Notes

Reaction equation

HRID 337697 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:33]=[C:34](/[CH:36]=[CH:37]/[CH2:38][O:39][CH3:40])[CH:35]=1)[CH2:5][N:6]([CH:30]1[CH2:32][CH2:31]1)[C:7]([C@H:9]1[C@H:14]([C:15]2[CH:20]=[CH:19][N:18]([CH3:21])[C:17](=[O:22])[CH:16]=2)[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)=[O:8].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:33]=[C:34](/[CH:36]=[CH:37]/[CH2:38][O:39][CH3:40])[CH:35]=1)[CH2:5][N:6]([CH:30]1[CH2:32][CH2:31]1)[C:7]([C@H:9]1[C@H:14]([C:15]2[CH:20]=[CH:19][N:18]([CH3:21])[C:17](=[O:22])[CH:16]=2)[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131732045HCID 131732045, compound

Product 1

HCID 87254190HCID 87254190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.1 M) of trans-tert-butyl 3-{[{3-bromo-5-[(1E)-3-methoxyprop-1-en-1-yl]benzyl}(cyclopropyl)amino]carbonyl}-4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)piperidine-1-carboxylate (1 eq.) from the previous step was added HCl (4.0 M dioxane solution, 30 eq.). The resulting solution was stirred at RT for 45 min. Following the removal of the volatiles in vacuo, the resulting residue was directly loaded onto a SiO2 column packed with 93:7 (v/v) CH2Cl2:2.0 M NH3 in MeOH. Elution with the same solvent system furnished the title compound. MS (ESI+, M+H): 516.

Workup

  1. customthe removal of the volatiles in vacuo
  2. washElution with the same solvent system

Sources & evidence

ORD record
ord-2d2efcd6b1974be8b144291e53075ac7
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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