Hydrochloric Acid → HCID 58314512, compound

HRID 624749Notes

Reaction equation

HRID 624749 reaction equation
C([NH:4][CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[C:16]([N:18]([CH:26]3[CH2:28][CH2:27]3)C(=O)OC(C)(C)C)[N:15]3[N:29]=[CH:30][C:31]([CH:32]=[O:33])=[C:14]3[N:13]=2)[CH:9]=[CH:10][CH:11]=1)(=O)C.Cl.[OH-].[Na+]>O1CCOCC1.O>[NH2:4][CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[C:16]([NH:18][CH:26]3[CH2:28][CH2:27]3)[N:15]3[N:29]=[CH:30][C:31]([CH:32]=[O:33])=[C:14]3[N:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58313817HCID 58313817, compound

Product 1

HCID 58314512HCID 58314512, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To tert-butyl 5-(3-(acetamidomethyl)phenyl)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (50 mg, 0.111 mmol) was added 1 mL of 4M HCl in 1,4-dioxane and 1 mL of H2O. The reaction mixture was stirred at 80° C. for 16 hours then cooled to room temperature and diluted with H2O. To the reaction mixture, 5M NaOH was added to adjust pH to >10 then the mixture was extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, filtered and evaporated to dryness to provide 24 mg of 5-(3-(aminomethyl)phenyl)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (70%). LCMS (M+1=308)

Workup

  1. temperaturethen cooled to room temperature
  2. extractionthe mixture was extracted with CH2Cl2
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1dcd95311f26467f857f38ff2da0b19b
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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