Hydrochloric Acid → HCID 57956118, compound

HRID 561891Notes

Reaction equation

HRID 561891 reaction equation
[CH:1]1([N:4]([CH2:37][C:38]2[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=2)[C:5](=[O:36])[CH:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][O:26][C:27]3[C:32]([Cl:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=3[Cl:35])=[CH:19][CH:18]=2)[CH2:7][NH:8]C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.Cl>C(Cl)Cl>[NH2:8][CH2:7][CH:6]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][O:26][C:27]2[C:32]([Cl:33])=[CH:31][C:30]([CH3:34])=[CH:29][C:28]=2[Cl:35])=[CH:21][CH:22]=1)[C:5]([N:4]([CH:1]1[CH2:2][CH2:3]1)[CH2:37][C:38]1[CH:39]=[CH:40][N:41]=[CH:42][CH:43]=1)=[O:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86635948tert-Butyl (3-[cyclopropyl(pyridin-4-ylmethyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Product 1

HCID 57956118HCID 57956118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.09 M) of tert-butyl (3-[cyclopropyl(pyridin-4-ylmethyl)amino]-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from the previous step (I eq.) was added HCl (4.0 M dioxane solution, 46 eq.). The resulting solution was stirred at RT for 5 h. The reaction was quenched with 2.0 M NH3 in MeOH and concentrated in vacuo. The resulting residue was directly loaded onto a SiO2 column packed with 90:9:1 (v/v) CH2Cl2:MeOH:conc. NH4OH. Elution with the same solvent system furnished the title compound. MS (ESI+): 527.9.

Workup

  1. customThe reaction was quenched with 2.0 M NH3 in MeOH
  2. concentrationconcentrated in vacuo
  3. washElution with the same solvent system

Sources & evidence

ORD record
ord-8c23addfe9bb45ab93d4e047f67a67df
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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