Dimethylformamide → HCID 67147945, compound

HRID 1864582Notes

Reaction equation

HRID 1864582 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:35])[C:23](OC3C=CC([N+]([O-])=O)=CC=3)=[O:24])[N:17]=2)=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2].CN(C)C=O.[CH2:41]([NH2:46])[CH2:42][CH2:43][CH2:44][CH3:45]>O>[CH2:1]([O:3][C@@H:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:35])[C:23]([NH:46][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:24])[N:17]=2)=[CH:14][CH:15]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8060PentylamineHCID 67148882HCID 67148882, compound

Product 1

HCID 67147945HCID 67147945, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.65 g (1.1 mmol) of methyl 2(S)-ethoxy-3-(4-{6-[methyl-(4-nitrophenoxycarbonyl)amino]pyrid-2-yl}phenyl)propanoate, 12 ml of dimethylformamide and 1 ml (8.8 mmol) of pentylamine are heated at 80° C. for 18 hours. After addition of water, the reaction medium is extracted with ethyl acetate. The ethyl acetate phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with a 7/3 and then 6/4 heptane/ethyl acetate mixture. 0.35 g (76%) of methyl 2(S)-ethoxy-3-{4-[6-(1-methyl-3-pentylureido)pyrid-2-yl]phenyl}propanoate is obtained.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. dry with materialThe ethyl acetate phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by thin-layer chromatography on silica
  7. washeluted with a 7/3

Sources & evidence

ORD record
ord-794e3c034acd487986d0e99baaa2def3
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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