Hydrochloric Acid → HCID 178429109, compound

HRID 2173910Notes

Reaction equation

HRID 2173910 reaction equation
[C:1]([C:3]1[CH:49]=[CH:48][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:10]([C:19]3[C:27]([O:28][CH:29]([F:31])[F:30])=[CH:26][C:25]([CH3:32])=[C:24]4[C:20]=3[CH:21]=[CH:22][N:23]4[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([NH:12]S(C(C)(C)C)=O)[CH3:11])=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(C3C(OC(F)F)=CC(C)=C4C=3C=CN4C(OC(C)(C)C)=O)(NS(C(C)(C)C)=O)C)N(COCC[Si](C)(C)C)C=2C=1)#N.Cl>>[NH2:12][C:10]([C:19]1[C:27]([O:28][CH:29]([F:31])[F:30])=[CH:26][C:25]([CH3:32])=[C:24]2[C:20]=1[CH:21]=[CH:22][N:23]2[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])([C:8]1[NH:7][C:6]2[CH:48]=[CH:49][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1)[CH3:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 86701447HCID 86701447, compoundHCID 86701448HCID 86701448, compound

Product 1

HCID 178429109HCID 178429109, compound

Procedure

To a mixture of (±)-tert-butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-(difluoromethoxy)-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-(difluoromethoxy)-7-methyl-1H-indole-1-carboxylate (306 mg, 0.427 mmol) was added HCl (1.25M in MeOH, 1.7 mL, 2.137 mmol) and the solution was stirred at room temperature for 90 minutes. The reaction mixture was then concentrated, diluted with sat. aq. NaHCO3, the aqueous layer was extracted with EtOAc, and the organic extract was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (0-80% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 482.3 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with sat. aq. NaHCO3
  3. extractionthe aqueous layer was extracted with EtOAc
  4. extractionthe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (0-80% EtOAc in heptanes)

Sources & evidence

ORD record
ord-61847772147442529e2161daf9f01675
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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