Hydrochloric Acid → 3-Amino-N-{[5-chloro-2-(methoxypropyl)-1-oxidopyridin-4-yl]methyl}-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide

HRID 561883Notes

Reaction equation

HRID 561883 reaction equation
[Cl:1][C:2]1[C:3]([CH2:14][N:15]([CH:48]2[CH2:50][CH2:49]2)[C:16](=[O:47])[CH:17]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][O:37][C:38]3[C:43]([Cl:44])=[CH:42][C:41]([CH3:45])=[CH:40][C:39]=3[Cl:46])=[CH:30][CH:29]=2)[CH2:18][NH:19]C(=O)OC(C)(C)C)=[CH:4][C:5]([CH2:9][CH2:10][CH2:11][O:12][CH3:13])=[N+:6]([O-:8])[CH:7]=1.Cl>C(Cl)Cl>[NH2:19][CH2:18][CH:17]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][O:37][C:38]2[C:43]([Cl:44])=[CH:42][C:41]([CH3:45])=[CH:40][C:39]=2[Cl:46])=[CH:30][CH:29]=1)[C:16]([N:15]([CH2:14][C:3]1[C:2]([Cl:1])=[CH:7][N+:6]([O-:8])=[C:5]([CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:4]=1)[CH:48]1[CH2:50][CH2:49]1)=[O:47]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 91035818HCID 91035818, compound

Product 1

HCID 159811813-Amino-N-{[5-chloro-2-(methoxypropyl)-1-oxidopyridin-4-yl]methyl}-N-cyclopropyl-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (0.07 M) of tert-butyl (3-[{[5-chloro-2-(methoxypropyl)-1-oxidopyridin-4-yl]methyl}(cyclopropyl)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 16 h. Following the removal of the volatiles in vacuo, the resulting residue was directly subjected to column chromatography (SiO2, 95:5 (v/v) CH2Cl2: 2.0 M NH3 in MeOH) to afford the title compound as an oil. MS (ESI+): 651.

Workup

  1. customthe removal of the volatiles in vacuo

Sources & evidence

ORD record
ord-4261ab71dd824d9599905af6b70d1698
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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