HCID 57678492, compound → HCID 57678512, compound

HRID 491680Notes

Reaction equation

HRID 491680 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([NH2:27])[CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:28][C:29]1[CH:41]=[CH:40][C:39]([N:42]=[C:43]=S)=[CH:38][C:30]=1[O:31][CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][O:34]1>CC#N.CN(C=O)C>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17]([O:19][C:20]3[CH:25]=[CH:24][C:23]4[O:26][C:43]([NH:42][C:39]5[CH:40]=[CH:41][C:29]([Cl:28])=[C:30]([O:31][CH2:32][CH:33]6[CH2:37][CH2:36][CH2:35][O:34]6)[CH:38]=5)=[N:27][C:22]=4[CH:21]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 57678492HCID 57678492, compoundHCID 86760863HCID 86760863, compound

Product 1

HCID 57678512HCID 57678512, 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 (4-pyrrolidin-1-yl-butyl)-amide (Step E, 162 mg, 0.438 mmol) in CH3CN (20 mL) and DMF (2 mL) was added 2-(2-chloro-5-isothiocyanato-phenoxymethyl)-tetrahydro-furan (112 mg, 0.417 mmol). The following day, the CH3CN was evaporated off, and the crude mix was diluted into 1 N 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 dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography to yield the title compound as a yellow solid. MS(MH+)=606.3; Calc'd 605.24 for C32H36ClN5O5.

Workup

  1. customThe following day, the CH3CN was evaporated off
  2. additionthe crude mix
  3. additionwas diluted into 1 N 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 dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-29ea69ab4c694370950a6f0035f2faaa
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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