Ammonium Chloride → HCID 59311442, compound

HRID 1693272Notes

Reaction equation

HRID 1693272 reaction equation
C[Mg]Br.ClC1N=C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)N=C2N(CC3C(C)=C(OC)C(C)=CN=3)N=C(CC=O)C=12.CC1C=CC(S([O:53][CH:54]([C:92]#N)[CH2:55][C:56]2[C:64]3[C:59](=[N:60][C:61]([N:66]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])=[N:62][C:63]=3[Cl:65])[N:58]([CH2:81][C:82]3[C:87]([CH3:88])=[C:86]([O:89][CH3:90])[C:85]([CH3:91])=[CH:84][N:83]=3)[N:57]=2)(=O)=O)=CC=1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[Cl:65][C:63]1[N:62]=[C:61]([N:66]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[C:67]([O:69][C:70]([CH3:72])([CH3:71])[CH3:73])=[O:68])[N:60]=[C:59]2[N:58]([CH2:81][C:82]3[C:87]([CH3:88])=[C:86]([O:89][CH3:90])[C:85]([CH3:91])=[CH:84][N:83]=3)[N:57]=[C:56]([CH2:55][CH:54]([OH:53])[CH3:92])[C:64]=12

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 59311456HCID 59311456, compoundHCID 59311568HCID 59311568, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59311442HCID 59311442, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 3 N solution of methylmagnesium bromide in diethyl ether (0.15 mL) was added dropwise to a mixture of di-tert-butyl {4-chloro-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-3-(2-oxoethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl}imidodicarbonate of Step 1) of Example 3 (120 mg) and dehydrated tetrahydrofuran (1 mL) under cooling in a dry ice-acetone bath, and then the mixture was stirred for one hour. A saturated ammonium chloride solution (1 mL) was added dropwise to the reaction mixture, and then the dry ice-acetone bath was removed. The reaction mixture was separated with ethyl acetate (30 mL) and water (30 mL). Then, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (ethyl acetate-hexane) to obtain the title compound (52 mg, 42%) as an oil.

Workup

  1. temperatureunder cooling in a dry ice-acetone bath
  2. customthe dry ice-acetone bath was removed
  3. customThe reaction mixture was separated with ethyl acetate (30 mL) and water (30 mL)
  4. washThen, the organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel thin-layer chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-a297c05c25834dc19a07e652a890b7b2
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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