Hydrochloric Acid → HCID 178509821, compound

HRID 2042841Notes

Reaction equation

HRID 2042841 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([NH:16][C:17]2[NH:43][C:20]3=[N:21][C:22]([O:38][CH2:39][CH:40]([F:42])[F:41])=[C:23]([C:25](=[O:37])[NH:26][C@H:27]4[CH2:32][CH2:31][C@H:30]([C:33]([F:36])([F:35])[F:34])[CH2:29][CH2:28]4)[CH:24]=[C:19]3[N:18]=2)[C:10]=1[Cl:44])(C)(C)C.Cl>O1CCOCC1.CO>[Cl:44][C:10]1[C:11]([NH:16][C:17]2[NH:43][C:20]3=[N:21][C:22]([O:38][CH2:39][CH:40]([F:41])[F:42])=[C:23]([C:25](=[O:37])[NH:26][C@H:27]4[CH2:32][CH2:31][C@H:30]([C:33]([F:36])([F:34])[F:35])[CH2:29][CH2:28]4)[CH:24]=[C:19]3[N:18]=2)=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[CH2:8][NH2:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178453058HCID 178453058, compound

Product 1

HCID 178509821HCID 178509821, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-{2,4-dichloro-3-[6-(trans-4-trifluoromethyl-cyclohexylcarbamoyl)-5-(2,2-difluoro-ethoxy)-3H-imidazo[4,5-b]pyridin-2-ylamino]benzyl}-carbamic acid tert-butyl ester (6.3 g, 9.3 mmol), 4 M HCl in dioxane (60 ml) and MeOH (5 ml) is stirred for 15 min. The mixture is concentrated, diluted with water and basified with conc. NH3. The precipitate is collected by filtration, washed with water, dried and purified via prep HPLC. The product fractions are concentrated, basified with conc. NH3, extracted with EtOAc. The organic phases are dried with Na2SO4 and concentrated to give the crude sub-title compound (4.8 g).

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with water and basified with conc. NH3
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water
  5. customdried
  6. custompurified via prep HPLC
  7. concentrationThe product fractions are concentrated
  8. extractionextracted with EtOAc
  9. dry with materialThe organic phases are dried with Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-082b7e34eb5a49d18c0c6cea6a4b60e6
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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