Hydrochloric Acid → HCID 86652654, compound

HRID 43026

Reaction equation

HRID 43026 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]([NH:5][CH:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][N:16]3[CH:20]=[C:19]([CH2:21][OH:22])[C:18]([C:23]([F:26])([F:25])[F:24])=[N:17]3)=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)=O.B#B.Cl>C1COCC1>[F:28][C:2]([F:1])([F:27])[CH2:3][NH:5][CH:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][N:16]3[CH:20]=[C:19]([CH2:21][OH:22])[C:18]([C:23]([F:24])([F:25])[F:26])=[N:17]3)=[CH:12][CH:13]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 445557322,2,2-Trifluoro-N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)acetamide

Product 1

HCID 86652654HCID 86652654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-(5-((4-(hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-2,3-dihydro-1H-inden-1-yl)acetamide (0.172 mmol, 70 mg) in THF (2 mL) was added diborane (1.719 mmol, 1.719 mL) and the whole heated to reflux for 6 h. The reaction mixture was allowed to cool to room temperature before being treated with 2N HCl (3 mL) and left to stand overnight. After this time the crude mixture was applied to an SCX column & eluted with 2N NH3/MeOH. After evaporation, the residue was further purified by prep LCMS to give a clear film (11 mg, 0.028 mmol, 16.3%). MS (ESI): m/z [M+H]+ 394.1.

Workup

  1. temperaturethe whole heated
  2. temperatureto reflux for 6 h
  3. waitleft
  4. washeluted with 2N NH3/MeOH
  5. customAfter evaporation
  6. customthe residue was further purified by prep LCMS
  7. customto give a clear film (11 mg, 0.028 mmol, 16.3%)

Sources & evidence

ORD record
ord-f7027af75a864385b6ed2b3a6210bce6
Source dataset
uspto-grants-2013_09
Patent number
US08536214B2

Linked notes

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