Hydrochloric Acid → HCID 67465955, compound

HRID 1019765Notes

Reaction equation

HRID 1019765 reaction equation
Cl.C(OC(=O)[N:8]([CH2:23][CH2:24][C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[N:41][C:40]([C:43]#[N:44])=[CH:39][N:38]=2)=[O:35])=[CH:27][C:26]=1[Cl:45])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)(C)(C)C.C(OCC)C>O1CCOCC1.C(#N)C>[ClH:45].[Cl:45][C:26]1[C:25]([CH2:24][CH2:23][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)=[CH:30][C:29]([O:31][CH3:32])=[C:28]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[N:41][C:40]([C:43]#[N:44])=[CH:39][N:38]=2)=[O:35])[CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 131731371HCID 131731371, compound

Product 1

HCID 67465955HCID 67465955, compoundYield 155.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A 3 N HCl solution in 1,4-dioxane (10 mL) was added to a stirred solution of tert-butyl-2-chloro-4-(3-(5-cyanopyrazin-2-yl)ureido)-5-methoxyphenethyl(4-(4-methylpiperazin-1-yl)benzyl)carbamate (0.5 g) in acetonitrile (50 mL) at 5° C. The reaction mixture was allowed to warm to room temperature and stirring continued for 1 hour. Diethylether (150 ml) was added and the precipitated solid collected by filtration. The solid was triturated with diethylether, methanol, diethylether then dried at reduced pressure to yield the title compound (0.35 g, 70%) as a yellow solid.

Workup

  1. filtrationthe precipitated solid collected by filtration
  2. customThe solid was triturated with diethylether, methanol, diethylether
  3. customthen dried at reduced pressure

Sources & evidence

ORD record
ord-c7fc0d231eb445c7978e4ca3c4a8d14c
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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