Ammonium Chloride → HCID 67407284, compound

HRID 869717Notes

Reaction equation

HRID 869717 reaction equation
CON(C)[C:4]([C:6]1[CH:33]=[C:9]2[N:10]=[C:11]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:12]=[C:13]([N:14]([CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:8]2[N:7]=1)=[O:5].[CH2:35]([Mg]Br)[CH3:36].[Cl-].[NH4+]>O1CCCC1>[C:4]([C:6]1[CH:33]=[C:9]2[N:10]=[C:11]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:12]=[C:13]([N:14]([CH:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:8]2[N:7]=1)(=[O:5])[CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86674520HCID 86674520, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 67407284HCID 67407284, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (2-{[methoxy(methyl)amino]carbonyl}-5-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidin-7-yl)tetrahydro-2H-pyran-4-ylcarbamate (2.22 g, 4.68 mmol) in tetrahydrofuran (50 mL) was added ethylmagnesium bromide solution (1M in tetrahydrofuran, 14.0 mL, 14.0 mmol) at 0° C. After being stirred for 20 min at same temperature, the reaction mixture was poured into saturated ammonium chloride. 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 to chloroform:ethyl acetate=3:2) to give tert-butyl (2-propionyl-5-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidin-7-yl)tetrahydro-2H-pyran-4-ylcarbamate. MS (APCI): m/z 444 (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 to chloroform:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-94c47812c28f47199ff215c79dbd5e5b
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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