Hydrochloric Acid → HCID 67061903, compound

HRID 337692Notes

Reaction equation

HRID 337692 reaction equation
[CH:1]1([N:4]([CH2:28][C:29]2[CH:30]=[C:31]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:32]=[C:33]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:34]=2)[C:5]([C@H:7]2[C@H:12]([C:13]3[CH:18]=[CH:17][N:16]([CH3:19])[C:15](=[O:20])[CH:14]=3)[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)=[O:6])[CH2:3][CH2:2]1.Cl>C(Cl)Cl>[CH:1]1([N:4]([CH2:28][C:29]2[CH:30]=[C:31]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:32]=[C:33]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:34]=2)[C:5]([C@H:7]2[C@H:12]([C:13]3[CH:18]=[CH:17][N:16]([CH3:19])[C:15](=[O:20])[CH:14]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131732041HCID 131732041, compound

Product 1

HCID 67061903HCID 67061903, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.05 M) of trans-tert-butyl 3-[(cyclopropyl{[5-(3-methoxypropyl)biphenyl-3-yl]methyl}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 as a white froth. MS (ESI+, M+H): 514. Human Renin IC50 (buffer): 15 nM. Human Renin IC50 (plasma): 81 nM.

Workup

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

Sources & evidence

ORD record
ord-f356a5c2dc4142c199a69d0539075aff
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…