Water → HCID 9831218, compound

HRID 1160429Notes

Reaction equation

HRID 1160429 reaction equation
O[CH2:2][CH2:3][N:4]([CH3:16])[C:5]1[N:10]=[C:9]([N:11]([CH3:15])[CH2:12][CH2:13]O)[CH:8]=[CH:7][CH:6]=1.[CH3:17][O:18][C:19](=[O:32])[CH:20]([O:29][CH2:30][CH3:31])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.[OH2:33]>C1COCC1>[CH3:17][O:18][C:19](=[O:32])[CH:20]([O:29][CH2:30][CH3:31])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][CH2:2][CH2:3][N:4]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([N:11]([CH2:12][CH2:13][S:28][C:25]3[CH:24]=[CH:23][C:22]([CH2:21][CH:20]([O:29][CH2:30][CH3:31])[C:19]([O:18][CH3:17])=[O:33])=[CH:27][CH:26]=3)[CH3:15])[N:10]=2)[CH3:16])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 16640757HCID 16640757, compound2×HCID 59515996HCID 59515996, compound2×

Product 1

HCID 9831218HCID 9831218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-({6-[(2-hydroxy-ethyl)-methyl-amino]-pyridin-2-yl}-methyl-amino)-ethanol (intermediate 4) (38 mg, 0.17 mmol) in dry THF (3.5 ml) was added at 0° C. under nitrogen tributylphosphine (100 mg, 0.50 mmol) and 2-ethoxy-3-(4-mercapto-phenyl)-propionic acid methyl ester (intermediate 2) (98 mg, 0.41 mmol). The reaction mixture was stirred for 15 min. and azodicarboxylic dipiperidine (126 mg, 0.50 mmol) was added. The reaction was stirred for 6 h, after which water (5 ml) was added and the mixture was extracted with methylene chloride (3×20 ml). The combined organic phases were dried (MgSO4), filtered and evaporated. The crude product was purified on column chromatograph using heptanes: ethyl acetate (3:1) as eluent to give the title compound in 85 mg (75%) yield.

Workup

  1. stirringThe reaction was stirred for 6 h
  2. extractionthe mixture was extracted with methylene chloride (3×20 ml)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified on column chromatograph

Sources & evidence

ORD record
ord-2c0b7feb8f2d4532bc36904b2bc21455
Source dataset
uspto-grants-2010_10
Patent number
US07816385B2

Reaction notes

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