Acetonitrile → HCID 86723380, compound

HRID 508544Notes

Reaction equation

HRID 508544 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([F:14])=[C:12]([NH:15]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:11]=[C:10]([CH:35](OCC)[O:36]CC)[N:9]=2)=[C:4]([F:42])[C:3]=1[O:43][CH3:44].CC#N>O>[NH2:15][C:12]1[C:13]([F:14])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:43][CH3:44])[C:4]=2[F:42])[N:9]=[C:10]([CH:35]=[O:36])[CH:11]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 86723379HCID 86723379, compound

Product 1

HCID 86723380HCID 86723380, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(4-chloro-2-fluoro-3-methoxyphenyl)-6-(diethoxymethyl)-3-fluoro-N-tritylpyridin-4-amine (2.117 g, 3.44 mmol), CH3CN (15 mL), water (15 mL) and 1 normal (N)H2SO4 (7.5 mL) was placed in an oil bath and heated to 80° C. After 2 h at 80° C., an aliquot of the reaction mixture was partitioned between EtOAc and 10% sodium bicarbonate (NaHCO3) and analyzed by high-performance liquid chromatography (HPLC) and TLC (80/20 hexanes/EtOAc). TLC and HPLC analyses showed only a trace of the starting material remaining (˜2% by HPLC) and essentially one, more polar product.

Workup

  1. customwas placed in an oil bath
  2. customan aliquot of the reaction mixture was partitioned between EtOAc and 10% sodium bicarbonate (NaHCO3)

Sources & evidence

ORD record
ord-75b27377452f49e8a690c713073b27c2
Source dataset
uspto-grants-2015_08
Patent number
US09096526B2

Reaction notes

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