Hydrochloric Acid → HCID 67062164, compound

HRID 337679Notes

Reaction equation

HRID 337679 reaction equation
[CH:1]1([N:4]([CH2:29][C:30]2[CH:35]=[C:34]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:33]=[C:32]([O:41][CH2:42][CH2:43][O:44][CH3:45])[CH:31]=2)[C:5]([C@H:7]2[C@H:12]([C:13]3[CH:18]=[CH:17][N:16]([CH2:19][CH3:20])[C:15](=[O:21])[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]([CH2:29][C:30]2[CH:35]=[C:34]([CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:33]=[C:32]([O:41][CH2:42][CH2:43][O:44][CH3:45])[CH:31]=2)[C:5]([C@H:7]2[C@H:12]([C:13]3[CH:18]=[CH:17][N:16]([CH2:19][CH3:20])[C:15](=[O:21])[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 131732028HCID 131732028, compound

Product 1

HCID 67062164HCID 67062164, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.07 M) of trans-1,1-dimethylethyl 3-{[cyclopropyl({3-{[2-(methyloxy)ethyl]oxy}-5-[3-(methyloxy)propyl]phenyl}methyl)amino]carbonyl}-4-(1-ethyl-2-oxo-1,2-dihydro-4-pyridinyl)-1-piperidinecarboxylate (1 eq.) from the previous step was added HCl (4.0 M dioxane solution, 30 eq.). The resulting solution was stirred at RT for 3 h. 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): 526. Human Renin IC50 (buffer): 200 nM. Human Renin IC50 (plasma): 460 nM.

Workup

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

Sources & evidence

ORD record
ord-e62336a30c394de79383c8048384675b
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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