Hydrochloric Acid → 3-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-[3-(3-methoxypropyl)-5-(2-pyridin-2-ylethoxy)benzyl]propanamide

HRID 561878Notes

Reaction equation

HRID 561878 reaction equation
[CH:1]1([N:4]([CH2:37][C:38]2[CH:43]=[C:42]([O:44][CH2:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=3)[CH:41]=[C:40]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[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:43]=[C:42]([O:44][CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=2)[CH:41]=[C:40]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[CH:39]=1)=[O:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86635939tert-Butyl (3-{cyclopropyl[3-(3-methoxypropyl)-5-(2-pyridin-2-ylethoxy)benzyl]amino}-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate

Product 1

HCID 159812523-Amino-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-N-[3-(3-methoxypropyl)-5-(2-pyridin-2-ylethoxy)benzyl]propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.03 M) of tert-butyl (3-{cyclopropyl[3-(3-methoxypropyl)-5-(2-pyridin-2-ylethoxy)benzyl]amino}-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}-3-oxopropyl)carbamate from the previous step (1 eq.) was added HCl (4.0 M dioxane solution, 30 eq.). The resulting solution was stirred at RT for 12 h. Following the removal of the volatiles in vacuo, the resulting residue was directly subjected to column chromatography (SiO2, 90:10 (v/v) CH2Cl2: 2.0 M NH3 in MeOH) to afford the title compound as a white froth. MS (ESI+): 720.0.

Workup

  1. customthe removal of the volatiles in vacuo

Sources & evidence

ORD record
ord-6ae1a20d51574caf9a8311e36ad3807e
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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