Hydrochloric Acid → HCID 178481215, compound

HRID 1189702Notes

Reaction equation

HRID 1189702 reaction equation
[F:1][C:2]([F:47])([F:46])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10]([C:12]2[C:39]([C:40]34[CH2:45][CH:44]3[CH2:43][NH:42][CH2:41]4)=[CH:38][C:15]3[N:16]([CH3:37])[C:17]([NH:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH2:27][NH:28]C(OC(C)(C)C)=O)[C:21]=4[Cl:36])=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH2:5][CH2:4]1.Cl>O1CCOCC1.CC(O)C>[F:47][C:2]([F:1])([F:46])[C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:9][C:10]([C:12]2[C:39]([C:40]34[CH2:45][CH:44]3[CH2:43][NH:42][CH2:41]4)=[CH:38][C:15]3[N:16]([CH3:37])[C:17]([NH:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH2:27][NH2:28])[C:21]=4[Cl:36])=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178481222HCID 178481222, compound2×

Product 1

HCID 178481215HCID 178481215, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-{2,6-dichloro-3-[(tert.-butoxycarbonylamino)-methyl]-phenylamino}-6-[3-aza-bicyclo[3.1.0]hex-1-yl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide (compound 185, 3.3 g, 4.7 mmol), 6 mL 4M HCl in dioxane, 10 mL dioxane and 5 mL 2-propanol is stirred overnight. The resulting precipitate is collected by filtration, diluted with EtOAc and washed with 1N aq NaOH. The organic phase is dried with Na2SO4, filtered and concentrated.

Workup

  1. filtrationThe resulting precipitate is collected by filtration
  2. additiondiluted with EtOAc
  3. washwashed with 1N aq NaOH
  4. dry with materialThe organic phase is dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63188278e66e43bf9c65f55e32e1b001
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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