HCID 17755615, compound → HCID 11454711, compound

HRID 491676Notes

Reaction equation

HRID 491676 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[OH:18])[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]([NH2:14])=[O:13])[CH:7]=1.[Cl:19][C:20]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=S)=[CH:30][C:21]=1[O:22][CH2:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[CH3:29]>CC#N.CN(C=O)C>[Cl:19][C:20]1[CH:33]=[CH:32][C:31]([NH:34][C:35]2[O:18][C:17]3[CH:16]=[CH:15][C:4]([O:5][C:6]4[CH:11]=[CH:10][N:9]=[C:8]([C:12]([NH2:14])=[O:13])[CH:7]=4)=[CH:3][C:2]=3[N:1]=2)=[CH:30][C:21]=1[O:22][CH2:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[CH3:29]

Participants

5

Reactant 2

HCID 17755615HCID 17755615, compoundHCID 17755842HCID 17755842, compound

Product 1

HCID 11454711HCID 11454711, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirring RT solution of 4-(3-amino-4-hydroxy-phenoxy)-pyridine-2-carboxylic acid amide (Step d, 217 mg, 0.884 mmol) in CH3CN (30 ml) and DMF (3 mL) was added (2S)-2-(2-chloro-5-isothiocyanato-phenoxymethyl)-1-methyl-pyrrolidine (208 mg, 0.737 mmol). The following day, the CH3CN was evaporated off, and the crude mix was diluted into 1N NaOH and EtOAc. The layers were separated. The aqueous layer was extracted 3× with EtOAc, and the combined organic layers were washed once with 1N NaOH and once with brine. The organic layer was then dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography to yield the title compound. (MH+)=494.2; Calc'd 493.15 for C25H24ClN5O4.

Workup

  1. customThe following day, the CH3CN was evaporated off
  2. additionthe crude mix
  3. additionwas diluted into 1N NaOH and EtOAc
  4. customThe layers were separated
  5. extractionThe aqueous layer was extracted 3× with EtOAc
  6. washthe combined organic layers were washed once with 1N NaOH and once with brine
  7. dry with materialThe organic layer was then dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2b5deaf51b03434aad43c6eec41e8706
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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