HCID 69299447, compound → HCID 71048311, compound

HRID 2196527Notes

Reaction equation

HRID 2196527 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[N:16]=[C:15]([CH2:17][NH2:18])[CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:19]([F:21])([F:20])[F:22])[CH:7]=1

Participants

3

Reactant 1

HCID 69299447HCID 69299447, compound

Product 1

HCID 71048311HCID 71048311, compoundYield 122.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
21 °C

Procedure

To a stirred solution of 46 (65 mg, 0.214 mmol) in THF (1.068 mL) was added 1M BH3 in THF (1.1 mL, 1.1 mmol). The resulting solution was allowed to stir at 21° C. for 3 hours. The excess BH3-THF was destroyed by the careful addition of MeOH. The solvent was evaporated, the residue dissolved in HCl/EtOH and the mixture was heated to reflux for 2 hours and then evaporated to dryness. The title product 47 (81 mg, 99% yield) was isolated as a pale yellow oil. LRMS (ESI): calc. 308.3; found 309.2 (MH)+.

Workup

  1. customThe excess BH3-THF was destroyed by the careful addition of MeOH
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in HCl/EtOH
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 2 hours
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ed078fef35f64c28b7201c7241eda6e9
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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