Hydrochloric Acid → HCID 178503114, compound

HRID 2173921Notes

Reaction equation

HRID 2173921 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]([C:27]1[N:31](COCC[Si](C)(C)C)[C:30]2[CH:40]=[CH:41][C:42]([C:44]#[N:45])=[CH:43][C:29]=2[N:28]=1)([OH:26])[C:4]1[C:12]([S:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].FC(F)(F)C(C1N(COCC[Si](C)(C)C)C2C=C(C#N)C=CC=2N=1)(O)C1C(SC)=CC(C)=C2C=1C=CN2S(C1C=CC(C)=CC=1)(=O)=O.Cl>>[F:47][C:2]([F:1])([F:46])[C:3]([C:27]1[NH:31][C:30]2[CH:40]=[CH:41][C:42]([C:44]#[N:45])=[CH:43][C:29]=2[N:28]=1)([OH:26])[C:4]1[C:12]([S:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:16]([C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[CH:24][CH:25]=1)(=[O:18])=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 86701467HCID 86701467, compoundHCID 86701468HCID 86701468, compound

Product 1

HCID 178503114HCID 178503114, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of (±)-2-(2,2,2-trifluoro-1-hydroxy-1-(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-(2,2,2-trifluoro-1-hydroxy-1-(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (246 mg, 0.351 mmol) was added HCl (1.25M in MeOH, 2.8 mL, 3.51 mmol) and the mixture was stirred at 60° C. After 30 minutes the reaction was cooled to room temperature, concentrated and basified with aq. NH4OH. The mixture was further diluted with MeOH. The resulting residue was purified directly by flash chromatography (0-80% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 571.1 (M+H).

Workup

  1. temperatureAfter 30 minutes the reaction was cooled to room temperature
  2. concentrationconcentrated and basified with aq. NH4OH
  3. additionThe mixture was further diluted with MeOH
  4. customThe resulting residue was purified directly by flash chromatography (0-80% EtOAc in heptanes)

Sources & evidence

ORD record
ord-707abe5732ce49b080095cfd5646f8ad
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…