Triethylamine → HCID 59278143, compound

HRID 559641Notes

Reaction equation

HRID 559641 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:10][C:11]([C:13]2[C:14]3[CH:21]=[N:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[C:15]=3[CH:16]=[N:17][CH:18]=2)=[O:12])[CH2:8][CH3:9])[CH2:2]1.CCN(CC)CC.C[Si]([N:40]=[C:41]=[O:42])(C)C>C(#N)C>[C:41]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:10][C:11]([C:13]2[C:14]3[CH:21]=[N:20][N:19]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[C:15]=3[CH:16]=[N:17][CH:18]=2)=[O:12])[CH2:8][CH3:9])[CH2:2]1)(=[O:42])[NH2:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 45137393HCID 45137393, compound

Product 1

HCID 59278143HCID 59278143, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (1-piperidin-3-yl-propyl)-amide (0.10 g, 0.26 mmol) in acetonitrile (1 mL) was added Et3N (79 μL, 0.79 mmol) followed by 85% trimethylsilyl isocyanate (125 μL, 0.784 mmol). After 4 hours, the cloudy mixture was filtered and attempts to crystallize the solid proved unsuccessful. The solid and filtrate was combined and diluted with water and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-10% methanol in dichloromethane to afford the title compound as a white solid.

Workup

  1. filtrationthe cloudy mixture was filtered
  2. customattempts to crystallize the solid
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a gradient of 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-112da10684be4daa83facf32157b6c03
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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