Thionyl Chloride → HCID 57527001, compound

HRID 1452587Notes

Reaction equation

HRID 1452587 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][C:14]=2[F:30])[CH:12]=1)=O>CN(C=O)C>[F:30][C:14]1[CH:15]=[C:16]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:17]=[CH:18][C:13]=1[N:11]1[CH:12]=[C:8]([C:6]#[N:5])[CH:9]=[N:10]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57527000HCID 57527000, compound2×

Product 1

HCID 57527001HCID 57527001, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (0.23 ml) was added to a stirred solution of benzyl 4-[4-(aminocarbonyl)-1H-pyrazol-1-yl]-3-fluorophenylcarbamate (Intermediate 40) (0.76 g, 2.14 mmol) in DMF (20 ml) at 0° C. The resulting mixture was warmed to room temperature and stirred for 1 hour. It was quenched with aqueous saturated sodium bicarbonate solution, extracted with ethyl acetate, dried over sodium sulfate and solvent was removed under vacuum to give the title product (0.71 g).

Workup

  1. customIt was quenched with aqueous saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate and solvent
  4. customwas removed under vacuum

Sources & evidence

ORD record
ord-8c6b39ab3f3f4281afcf9e70b18d46ce
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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