Water → HCID 67047584, compound

HRID 606886Notes

Reaction equation

HRID 606886 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[CH:20]=1)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].O>ClCCl>[NH2:14][C:15]1[CH:20]=[C:19]([C:21]#[C:22][C:23]2[CH:24]=[C:25]([CH:26]=[CH:27][CH:28]=2)[C:29]#[N:30])[CH:18]=[N:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 67047441HCID 67047441, compound

Product 1

HCID 67047584HCID 67047584, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (1 mL, 13.3 mmol) to a solution of [5-(3-cyanophenylethynyl)-pyridin-3-yl]-carbamic acid tert-butyl ester, prepared as described in EXAMPLE 125), (315 mg, 0.99 mmol) in dichloromethane (5 mL) and stir for 4 h. Add solid potassium carbonate to the reaction mixture until basic (pH=8) and then water to give a biphasic solution. Separate the layers, load the aqueous layer onto an ISOLUTE™ phase separator cartridge and wash the cartridge with dichloromethane (3×15 mL). Concentrate and purify the residue by silica gel chromatography, eluting with 25:75 to 0:100 with dichloromethane:ethyl acetate, to give the title compound (190 mg, 88%).

Workup

  1. customprepared
  2. customSeparate the layers, load the aqueous layer onto an ISOLUTE™ phase separator cartridge
  3. washwash the cartridge with dichloromethane (3×15 mL)
  4. concentrationConcentrate
  5. custompurify the residue by silica gel chromatography
  6. washeluting with 25:75 to 0:100 with dichloromethane

Sources & evidence

ORD record
ord-5b34f8fed1d042908ee2e120ef1beee2
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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