Hydrochloric Acid → HCID 178435788, compound

HRID 2174007Notes

Reaction equation

HRID 2174007 reaction equation
[CH2:1]([C:3]1[C:4]([C:23]([C:29]2[N:33](COCC[Si](C)(C)C)[C:32]3[CH:42]=[CH:43][C:44]([C:46]#[N:47])=[CH:45][C:31]=3[N:30]=2)([OH:28])[C:24]([F:27])([F:26])[F:25])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:7]=[CH:6]2)[CH3:2].C(C1C(C(C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)(O)C(F)(F)F)=C2C(=C(C)C=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2)C.Cl.CO>>[CH2:1]([C:3]1[C:4]([C:23]([C:29]2[NH:33][C:32]3[CH:42]=[CH:43][C:44]([C:46]#[N:47])=[CH:45][C:31]=3[N:30]=2)([OH:28])[C:24]([F:26])([F:27])[F:25])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:7]=[CH:6]2)[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86701591HCID 86701591, compoundHCID 86701592HCID 86701592, compound

Product 1

HCID 178435788HCID 178435788, compound

Conditions

Temperature
60 °C

Procedure

A mixture of (±)-2-(1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)-2,2,2-trifluoro-1-hydroxyethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-(1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)-2,2,2-trifluoro-1-hydroxyethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (1.16 g, 1.69 mmol) and HCl in MeOH (1.25 M, 13.59 mL, 16.99 mmol) was allowed to stir at 60° C. for 0.5 h. The reaction mixture was cooled to rt and concentrated. The residue was dissolved in a small amount of EtOAc, and then diluted with heptanes. The precipitated solid was collected on a Kiriyama funnel, washed with hexane, dried under reduced pressure to give the title compound. MS (ESI+) m/z 553.3 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in a small amount of EtOAc
  4. additiondiluted with heptanes
  5. customThe precipitated solid was collected on a Kiriyama funnel
  6. washwashed with hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-d5f8caaa2b48450ea726faab769a5a9d
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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