Hydrochloric Acid → 1-(5-Chloro-2-methoxy-4-(2-(4-(piperazin-1-yl)benzylamino)ethyl)phenyl)-3-(5-cyanopyrazin-2-yl)urea dihydrochloride

HRID 1019782Notes

Reaction equation

HRID 1019782 reaction equation
[ClH:1].C(OC([N:9]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]2[CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42][CH2:41]2)=[CH:36][CH:35]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[N:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)=[O:22])=[CH:14][C:13]=1[Cl:32])=O)(C)(C)C.C(OCC)C>O1CCOCC1.C(#N)C>[ClH:32].[ClH:1].[Cl:32][C:13]1[C:12]([CH2:11][CH2:10][NH:9][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([N:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)=[CH:36][CH:35]=2)=[CH:17][C:16]([O:18][CH3:19])=[C:15]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[N:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)=[O:22])[CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67465989Tert-butyl 4-(4-((tert-butoxycarbonyl (2-chloro-4-(3-(5-cyanopyrazin-2-yl) ureido)-5-methoxy-phenethyl)amino)methyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 674678821-(5-Chloro-2-methoxy-4-(2-(4-(piperazin-1-yl)benzylamino)ethyl)phenyl)-3-(5-cyanopyrazin-2-yl)urea dihydrochlorideYield 60%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A 3 N HCl solution in 1,4-dioxane (0.4 mL) was slowly added to a solution of tert-butyl 4-(4-((tert-butoxycarbonyl (2-chloro-4-(3-(5-cyanopyrazin-2-yl)ureido)-5-methoxy-phenethyl)amino)methyl)phenyl)piperazine-1-carboxylate (0.1 g) in acetonitrile (5 mL) at 0° C. The mixture was allowed to warm to room temperature and then stirring continued for one hour. Diethyl ether (25 mL) was added and after stirring continued for 15 minutes then the supernatant was decanted and the resulting solid was triturated with diethyl ether (25 mL) and dried under reduced pressure to yield a yellow solid. The solid was further triturated with methanol followed by diethyl ether and dried under reduced pressure to give the title compound (0.05 g, 60%) as an off-white solid.

Workup

  1. stirringafter stirring
  2. waitcontinued for 15 minutes
  3. customthe supernatant was decanted
  4. customthe resulting solid was triturated with diethyl ether (25 mL)
  5. customdried under reduced pressure
  6. customto yield a yellow solid
  7. customThe solid was further triturated with methanol
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-bf48de8fe13843ccb444facf42fb5b15
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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