Hydrochloric Acid → HCID 21938699, compound

HRID 1242711Notes

Reaction equation

HRID 1242711 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH3:35])[C:14](=O)[CH:15]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[O:22])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1.Cl.[OH-].[Na+]>C1COCC1>[NH3:8].[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH2:14][CH:15]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=2)=[O:22])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:35])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 21938697HCID 21938697, compound

Product 2

HCID 222AmmoniaYield 2%HCID 21938699HCID 21938699, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8 (55 mg, 0.112 mmol) in THF (0.51 mL) was added 1.0 M BH3-THF (340 μL, 0.340 mmol) and the reaction heated to 50° C. for 22 hours. The reaction temperature was then increased to 80° C. and the reaction allowed to continue for an additional 24 hours. After cooling to room temperature, 2 M aqueous HCl (approx. 1 mL) was added to the reaction and the solution allowed to stir for one and one half hours. Next, the solution was basified with aqueous 2 M NaOH and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was then purified by flash column chromatography using silica gel and a gradient of 2 to 5% 2.0 M NH3 in EtOH/DCM to provide pure 9 (15 mg, 28%). LRMS calculated for C26H35F3N4O 476.28. Found 476.03.

Workup

  1. temperatureThe reaction temperature was then increased to 80° C.
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with DCM
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was then purified by flash column chromatography

Sources & evidence

ORD record
ord-1b1b0929925a465fab0bef77e895f614
Source dataset
uspto-grants-2006_10
Patent number
US07115664B2

Reaction notes

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