Water → HCID 57703747, compound

HRID 1632051Notes

Reaction equation

HRID 1632051 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17](O)=O)[C:9]=2[F:20])[CH:5]=[CH:6][CH:7]=1.[NH2:21][NH:22][C:23]([NH2:25])=[S:24].O>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[S:24][C:23]([NH2:25])=[N:22][N:21]=3)[C:9]=2[F:20])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723789ThiosemicarbazideHCID 58020306HCID 58020306, compound

Product 1

HCID 57703747HCID 57703747, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (3′-Chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-acetic acid (I-79) (0.998 mmol, 1.0 eq.) and thiosemicarbazide (2.99 mmol; 3 eq.) in excess phosphorous oxychloride was heated to 120° C. for 45 minutes, and allowed to cool to room temperature. The resultant mixture was added to water, and extracted with 2 portions of ethyl acetate. The organics were washed with brine, and dried over magnesium sulfate. The residue was purified via flash chromatography on silica gel using 5% (1N NH3 in MeOH) in dichloromethane as eluent to afford the desired product (P-333) in 39% yield.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with 2 portions of ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe residue was purified via flash chromatography on silica gel using 5% (1N NH3 in MeOH) in dichloromethane as eluent

Sources & evidence

ORD record
ord-129a02f3c95940cbbbfdd701c652d000
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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