Hydrochloric Acid → HCID 178494645, compound

HRID 2173923Notes

Reaction equation

HRID 2173923 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]([C:28]1[N:32](COCC[Si](C)(C)C)[C:31]2[CH:41]=[CH:42][C:43]([C:45]#[N:46])=[CH:44][C:30]=2[N:29]=1)([O:26][CH3:27])[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)(OC)C1C(SC)=CC(C)=C2C=1C=CN2S(C1C=CC(C)=CC=1)(=O)=O.Cl>>[F:48][C:2]([F:1])([F:47])[C:3]([C:28]1[NH:32][C:31]2[CH:41]=[CH:42][C:43]([C:45]#[N:46])=[CH:44][C:30]=2[N:29]=1)([O:26][CH3:27])[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 86701471HCID 86701471, compoundHCID 86701472HCID 86701472, compound

Product 1

HCID 178494645HCID 178494645, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of (±)-2-(2,2,2-trifluoro-1-methoxy-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-methoxy-1-(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)ethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (265 mg, 0.371 mmol) was added HCl (1.25M in MeOH, 2.9 mL, 3.71 mmol) and the mixture was stirred at 60° C. After 20 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 585.1 (M+H).

Workup

  1. temperatureAfter 20 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-3a81f05ee30a4adb9088ead35109c46f
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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