Ammonia → HCID 49819238, compound

HRID 1020753Notes

Reaction equation

HRID 1020753 reaction equation
C(OC([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[C:18]([N:23]([CH3:38])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)[CH:26]=2)[CH:17]=[N:16]3)[CH:10]=[N:9]1)=O)(C)(C)C.Cl.N>O1CCOCC1.C1COCC1>[CH3:38][N:23]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]2[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]2)[CH:26]=1)[C:18]1[CH:17]=[N:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:11]3[CH:12]=[N:8][NH:9][CH:10]=3)[CH:14]=2)[N:19]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 66797599HCID 66797599, compound

Product 1

HCID 49819238HCID 49819238, compoundYield 56,501.699%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 4-(2-{Methyl-[3-(4-methyl-piperazin-1-yl)-benzyl]-amino}-quinoxalin-6-yl)-pyrazole-1-carboxylic acid tert-butyl ester (0.110 g, 0.000214 mmol) in 1,4-dioxane (1.5 mL), was added HCl in dioxane (1.0 ml) at room temperature. The mixture was stirred for 1 hour. After completion of the reaction, the reaction mixture was concentrated and washed with diethyl ether (5.0 mL) to afford the crude compound (0.075 g). The compound was basified by ammonia in THF and then further purified by preparative TLC to afford the title compound (0.050 g, 54%). The mobile phase used for the Preparative TLC was DCM:Methanol (9:1).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. washwashed with diethyl ether (5.0 mL)
  4. customto afford the crude compound (0.075 g)
  5. customfurther purified by preparative TLC

Sources & evidence

ORD record
ord-cb0a0537b15149e29d2a4c564572427e
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

Loading…