Hydrochloric Acid → HCID 178510130, compound

HRID 450341Notes

Reaction equation

HRID 450341 reaction equation
[F:1][C:2]([F:48])([F:47])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[N:27]=[C:26]([NH:28][C:29]4[C:34]([Cl:35])=[C:33]([F:36])[CH:32]=[C:31]([CH2:37][NH:38]C(OC(C)(C)C)=O)[C:30]=4[Cl:46])[NH:25][C:15]3=[N:16][C:17]=2[N:18]2[CH2:23][CH2:22][CH:21]([F:24])[CH2:20][CH2:19]2)=[O:11])[CH2:5][CH2:4]1.Cl>O1CCOCC1>[F:47][C:2]([F:1])([F:48])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[N:27]=[C:26]([NH:28][C:29]4[C:34]([Cl:35])=[C:33]([F:36])[CH:32]=[C:31]([CH2:37][NH2:38])[C:30]=4[Cl:46])[NH:25][C:15]3=[N:16][C:17]=2[N:18]2[CH2:19][CH2:20][CH:21]([F:24])[CH2:22][CH2:23]2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178453092HCID 178453092, compound

Product 1

HCID 178510130HCID 178510130, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-{2,6-dichloro-5-fluoro-3-[(tert.butoxycarbonylamino)-methyl]-phenylamino}-5-[4-fluoro-piperidinyl]-3H-imidazo[4,5-b]pyridine-6-carboxamide (180 mg, 0.250 mmol), 4N HCl in dioxane (5.0 mL) and dioxane (10 mL) is stirred overnight, concentrated, dissolved in water, filtered, basicified with aq NH3-solution and extracted with DCM. The organic phase is dried with MgSO4, filtered and concentrated.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in water
  3. filtrationfiltered
  4. extractionextracted with DCM
  5. dry with materialThe organic phase is dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9382b634ded846c390efdee9dbd64d2e
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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