Hydrochloric Acid → HCID 67061970, compound

HRID 337684Notes

Reaction equation

HRID 337684 reaction equation
[CH:1]1([N:4]([CH2:30][C:31]2[CH:36]=[C:35]([CH2:37][CH2:38][CH2:39][O:40][CH3:41])[CH:34]=[C:33]([O:42][CH2:43][CH2:44][O:45][CH3:46])[CH:32]=2)[C:5]([C@H:7]2[C@H:12]([C:13]3[C:18]([CH3:19])=[C:17]([CH3:20])[N:16]([CH3:21])[C:15](=[O:22])[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]([CH2:30][C:31]2[CH:36]=[C:35]([CH2:37][CH2:38][CH2:39][O:40][CH3:41])[CH:34]=[C:33]([O:42][CH2:43][CH2:44][O:45][CH3:46])[CH:32]=2)[C:5]([C@H:7]2[C@H:12]([C:13]3[C:18]([CH3:19])=[C:17]([CH3:20])[N:16]([CH3:21])[C:15](=[O:22])[CH:14]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131732033HCID 131732033, compound

Product 1

HCID 67061970HCID 67061970, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.06 M) of trans-1,1-dimethylethyl 3-{[cyclopropyl({3-{[2-(methyloxy)ethyl]oxy}-5-[3-(methyloxy)propyl]phenyl}methyl)amino]carbonyl}-4-(1,5,6-trimethyl-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 4 h. Following the removal of the volatiles in vacuo, the resulting residue was directly loaded onto a SiO2 column packed with 94:6 (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): 540. Human Renin IC50 (buffer): 25 nM. Human Renin IC50 (plasma): 80 nM.

Workup

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

Sources & evidence

ORD record
ord-162e5c96722c4fcba31423bba20614cb
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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