Hydrochloric Acid → HCID 58986326, compound

HRID 420802Notes

Reaction equation

HRID 420802 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17]COC)=[CH:14][CH:15]=2)[C:10]([CH2:21][NH:22][CH2:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=2)=[C:9]1[CH:32]([CH3:34])[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)(C)C.C1COCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([CH2:21][NH:22][CH2:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=2)=[C:9]1[CH:32]([CH3:34])[CH3:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58986328HCID 58986328, compound2×

Product 1

HCID 58986326HCID 58986326, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(1-benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indol-3-yl)-N-(3,5-difluorobenzyl)methanamine (Compound 5, 117 mg, 0.25 mmol) in isopropanol (2.0 ml) and THF (2.0 ml) was added 6 M HCl (0.4 ml). The mixture was stirred at room temperature for 16 h, and concentrated under vacuum. The mixture was diluted with EtOAc, and washed with phosphate buffer (pH=7.2), and brine, and dried over Na2SO4, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with 20-60% EtOAc-hexanes to yield 1-benzyl-3-((3,5-difluorobenzylamino)methyl)-2-isopropyl-1H-indol-5-ol (Compound 6) as a yellow solid.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with phosphate buffer (pH=7.2), and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography on silica gel eluting with 20-60% EtOAc-hexanes

Sources & evidence

ORD record
ord-9a9f8720f18e4466b45d0612a687c713
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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