Water → HCID 121317228, compound

HRID 59129Notes

Reaction equation

HRID 59129 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([CH2:22][C:23]([O:25]CC)=O)[CH:19]=[C:18]([CH2:28][O:29][CH2:30][C:31]([F:34])([F:33])[F:32])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[C-]#[N:36].[K+].O>[OH-].[NH4+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([CH2:22][C:23]([NH2:36])=[O:25])[CH:19]=[C:18]([CH2:28][O:29][CH2:30][C:31]([F:33])([F:34])[F:32])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 117824027HCID 117824027, compound

Product 1

HCID 121317228HCID 121317228, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 2-(2-{[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]amino}-6-[(2,2,2-trifluoro-ethoxy)methyl]pyrimidin-4-yl)acetate (140 mg, 0.30 mmol, 1.0 eq) was suspended in ammonium hydroxide (3 mL) with few crystals of potassium cyanide in a sealed tube. The mixture was stirred 4 days at 65° C. The reaction mixture was cooled down to rt, water was added and the aqueous layer was extracted with DCM (5×). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified on a silica gel cartridge eluting with 0% to 10% MeOH/DCM (1% ammonium hydroxide) to give the title compound as a solid, 68 mg (50%).

Workup

  1. temperatureThe reaction mixture was cooled down to rt
  2. extractionthe aqueous layer was extracted with DCM (5×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel cartridge
  6. washeluting with 0% to 10% MeOH/DCM (1% ammonium hydroxide)

Sources & evidence

ORD record
ord-7bd88d2e026f42b2afec9bf1f5ef9056
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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