Hydrochloric Acid → trans-N-Cyclopropyl-N-[3-[2-(cyclopropyloxy)ethoxy]-5-(3-methoxypropyl)benzyl]-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide

HRID 337700Notes

Reaction equation

HRID 337700 reaction equation
[CH:1]1([N:4]([CH2:28][C:29]2[CH:34]=[C:33]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:32]=[C:31]([O:40][CH2:41][CH2:42][O:43][CH:44]3[CH2:46][CH2:45]3)[CH:30]=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:34]=[C:33]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:32]=[C:31]([O:40][CH2:41][CH2:42][O:43][CH:44]3[CH2:45][CH2:46]3)[CH:30]=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 131732047trans-tert-Butyl 3-({cyclopropyl[3-[2-(cyclopropyloxy)ethoxy]-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-1-piperidinecarboxylate

Product 1

HCID 66896625trans-N-Cyclopropyl-N-[3-[2-(cyclopropyloxy)ethoxy]-5-(3-methoxypropyl)benzyl]-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.1 M) of trans-tert-butyl 3-({cyclopropyl[3-[2-(cyclopropyloxy)ethoxy]-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-(1-methyl-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 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): 538.

Workup

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

Sources & evidence

ORD record
ord-fcd5acb07b094822b57da3f1fe846a38
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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