Methyl chloroformate → HCID 59139482, compound

HRID 2061144Notes

Reaction equation

HRID 2061144 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.[OH:8][C:9]1[CH:17]=[C:16]([O:18][C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O.ClC(OC)=[O:27].NCCC1[C:34]([F:40])=[C:35]([NH2:39])[CH:36]=[CH:37][CH:38]=1>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[NH2:39][C:35]1[C:34]([F:40])=[C:7]([CH:38]=[CH:37][CH:36]=1)[CH2:6][N:3]1[C:11](=[O:13])[C:10]2[CH:14]=[CH:15][C:16]([O:18][C:19]3[N:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:17][C:9]=2[O:8][C:4]1=[O:27]

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 8471Triethylamine2×HCID 59139401HCID 59139401, compoundHCID 66857987HCID 66857987, compound

Product 1

HCID 59139482HCID 59139482, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

Triethylamine (0.180 mL, 1.29 mmol) was added to a mixture of 2-hydroxy-4-(pyrimidin-2-yloxy)benzoic acid (100 mg, 0.431 mmol) and chloroform (5.0 mL) at room temperature. The dark brown solution was cooled to 4° C., and methyl chloroformate (0.073 mL, 0.945 mmol) was then added thereto. The resulting light purple solution was stirred at room temperature for 2.5 hours and concentrated under reduced pressure. It was then redissolved in chloroform (5.0 mL), and a solution of triethylamine (0.120 mL, 0.861 mmol) and 3-aminoethyl-2-fluoro-phenylamine (60.0 mg, 0.428 mmol) in chloroform (1.0 mL) was added thereto. The obtained mixture was stirred at room temperature for 64 hours. Water was then added to the reaction mixture, and extraction was performed with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate, and then again washed with saturated saline. After drying over magnesium sulfate, it was concentrated under reduced pressure to yield a crude product, which was then purified by column chromatography to yield the title compound (25.8 mg, 16%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionIt was then redissolved in chloroform (5.0 mL)
  3. stirringThe obtained mixture was stirred at room temperature for 64 hours
  4. extractionThe organic extract
  5. washwas washed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. washagain washed with saturated saline
  8. dry with materialAfter drying over magnesium sulfate, it
  9. concentrationwas concentrated under reduced pressure
  10. customto yield a crude product, which
  11. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-67d69043dad0452884bd4acf680f82a9
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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