Hydrochloric Acid → HCID 67394792, compound

HRID 869718Notes

Reaction equation

HRID 869718 reaction equation
[C:1]([C:5]1[CH:32]=[C:8]2[N:9]=[C:10]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:11]=[C:12]([N:13]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)C(=O)OC(C)(C)C)[N:7]2[N:6]=1)(=[O:4])[CH2:2][CH3:3].N([O-])=[O:34].[Na+].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[N:27]1([C:10]2[CH:11]=[C:12]([NH:13][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:7]3[N:6]=[C:5]([C:1](=[O:4])[C:2](=[O:34])[CH3:3])[CH:32]=[C:8]3[N:9]=2)[CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 67407284HCID 67407284, compound

Product 1

HCID 67394792HCID 67394792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of tert-butyl (2-propionyl-5-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidin-7-yl)tetrahydro-2H-pyran-4-ylcarbamate (500 mg, 1.13 mmol) and sodium nitrite (233 mg, 3.38 mmol) in tetrahydrofuran (10 mL) was added conc. hydrochloric acid solution (36%, 5.0 mL) at 0° C. After being stirred for 20 h at room temperature, the reaction mixture was poured into saturated sodium bicarbonate. The mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform:ethyl acetate=1:1 to 1:9) to give 1-[5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)-pyrazolo[1,5-a]pyrimidin-2-yl]propane-1,2-dione. MS (APCI): m/z 358 (M+H).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by silica gel column chromatography (chloroform:ethyl acetate=1:1 to 1:9)

Sources & evidence

ORD record
ord-f440c012dfe74e90b704ac0e77020a7c
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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