Hydrochloric Acid → HCID 58515955, compound

HRID 717837Notes

Reaction equation

HRID 717837 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:27]=[N:28][CH:29]=2)[C:5]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[C:6]([C:8](N(OC)C)=[O:9])[CH:7]=1.[CH3:30][Mg]Cl.Cl.O.C([O-])(O)=O.[Na+]>O1CCCC1>[C:8]([C:6]1[CH:7]=[C:2]([Cl:1])[C:3]2[N:4]([CH:27]=[N:28][CH:29]=2)[C:5]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=[O:9])[CH3:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 58515975HCID 58515975, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 58515955HCID 58515955, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a microwave vial was placed a solution of tert-butyl 4-(8-chloro-6-{[methoxy(methyl)amino]carbonyl}imidazo[1,5-a]pyridin-5-yl)piperazine-1-carboxylate (31 mg, 0.073 mmol) in anhydrous tetrahydrofuran (0.5 mL) under N2 at 0° C. A solution of 3.0 M methylmagnesium chloride in tetrahydrofuran (85 μL, 0.26 mmol) was added dropwise. The solution was stirred at 0° C. for 30 minutes. It was stirred for 2 hours at room temperature. The reaction solution was quenched at 0° C. with 1.0 M hydrogen chloride in water (0.5 mL, 0.5 mmol), poured into 25 mL of saturated NaHCO3 solution and was extracted into ethyl acetate. The ethyl acetate extract was washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated to give the crude which was purified on silica gel with ethyl acetate (0-60%) to give desired product (22 mg, 78%). LCMS calculated for C18H24ClN4O3 (M+H)+: m/z=379.2. found: 378.9.

Workup

  1. customat 0° C
  2. stirringIt was stirred for 2 hours at room temperature
  3. extractionwas extracted into ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude which
  10. customwas purified on silica gel with ethyl acetate (0-60%)

Sources & evidence

ORD record
ord-7f231fd7a5b04f1c84374ed0b48df13a
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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