Hydrochloric Acid → HCID 21091065, compound

HRID 351244Notes

Reaction equation

HRID 351244 reaction equation
Cl.[NH2:2][C:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:18]=[C:17]([NH:28]C(=O)OC(C)(C)C)[CH:16]=2)=[CH:11][CH:10]=1)=[O:4]>O1CCOCC1.C(Cl)Cl>[NH4+:2].[OH-:4].[NH2:28][C:17]1[CH:16]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][NH:5][C:3]([NH2:2])=[O:4])=[CH:10][CH:11]=2)[N:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:18]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86592856HCID 86592856, compound

Product 2

HCID 14923Ammonium HydroxideYield 28%HCID 21091065HCID 21091065, compoundYield 130.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4M solution of HCl in dioxane (3 ml) was added to a solution of tert-butyl [5-(4-{2-[(aminocarbonyl)amino]ethoxy}-phenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]carbamate (478 mg) in CH2Cl2 (3 ml) The reaction mixture was stirred at ambient temperature for 5 hours and concentrated in vacuo. The residue was partitioned between CDCl3 and saturated aqueous sodium bicarbonate solution. The aq layer was reextrated with CHCl3. The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with CHCl3:MeOH:28% aqueous NH4OH=10:1:0.1 to give N-(2-{4-[3-amino-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)urea (244.6 mg) as an amorphous powder.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between CDCl3 and saturated aqueous sodium bicarbonate solution
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with CHCl3

Sources & evidence

ORD record
ord-e8725c18338042919ee10b6e7eca0531
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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