Water → HCID 71539570, compound

HRID 1466215Notes

Reaction equation

HRID 1466215 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([N:14]([CH2:30][C:31]3[CH:32]=[C:33]4[C:48]([CH3:49])=[N:47][N:46]([C:50]([CH3:53])([CH3:52])[CH3:51])[C:34]4=[N:35][C:36]=3[N:37]([CH2:42][CH:43]3[CH2:45][CH2:44]3)[CH2:38][CH:39]3[CH2:41][CH2:40]3)[CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)=[N:12][CH:13]=2)=[N:4]1.[CH3:54]I.O>CN(C=O)C>[F:27][C:26]([F:28])([F:29])[C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=1)[CH2:15][N:14]([CH2:30][C:31]1[CH:32]=[C:33]2[C:48]([CH3:49])=[N:47][N:46]([C:50]([CH3:53])([CH3:52])[CH3:51])[C:34]2=[N:35][C:36]=1[N:37]([CH2:42][CH:43]1[CH2:45][CH2:44]1)[CH2:38][CH:39]1[CH2:41][CH2:40]1)[C:11]1[N:10]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][N:3]([CH3:54])[N:4]=2)=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178434032HCID 178434032, compound

Product 1

HCID 71539570HCID 71539570, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.008 g, 0.21 mmol) in DMF (2 ml) was added dropwise with stirring to 5-(((5-(1H-pyrazol-3-yl)pyrimidin-2-yl)(3,5-bis(trifluoromethyl)benzyl)amino)methyl)-1-(tert-butyl)-N,N-bis(cyclopropylmethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-6-amine, obtained in Example 8 (0.03 g, 0.042 mmol). The reaction mixture was stirred for 20 min at 0° C. CH3I was added at this temperature and the mixture was stirred for an hour at 20-35° C. The reaction mixture was then treated with water and the mixture was extracted three times with ethyl acetate (50 ml). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to get the crude product. The crude product was further purified by column chromatography using 60-120 silica gel and 35% EtOAc in petroleum ether as eluent to afford the title compound.

Workup

  1. stirringthe mixture was stirred for an hour at 20-35° C
  2. extractionthe mixture was extracted three times with ethyl acetate (50 ml)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto get the crude product
  7. customThe crude product was further purified by column chromatography

Sources & evidence

ORD record
ord-1a5681e0787543f7bd7e237780ddba17
Source dataset
uspto-grants-2015_04
Patent number
US09000007B2

Reaction notes

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