1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 3-[4-(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)phenyl]propanoate

HRID 1099680Notes

Reaction equation

HRID 1099680 reaction equation
[NH2:1][C:2]1[C:10]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([C:22]3[O:23][CH:24]=[CH:25][C:26]=3[CH3:27])=[O:21])[CH:14]=2)=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.CCN=C=NCCCN(C)C.[CH3:39][S:40]([C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52])=[CH:45][CH:44]=1)(=[NH:42])=[O:41]>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:42]=[S:40]([C:43]2[CH:44]=[CH:45][C:46]([CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52])=[CH:47][CH:48]=2)([CH3:39])=[O:41])=[O:7])=[CH:9][C:10]=1[C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]([C:22]2[O:23][CH:24]=[CH:25][C:26]=2[CH3:27])=[O:21])[CH:14]=1

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 57657822Methyl 3-[4-(S-methylsulfonimidoyl)phenyl]propanoateHCID 576578956-Amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acid

Product 1

HCID 57657818Methyl 3-[4-(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)phenyl]propanoateYield 37%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

6-Amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acid (0.1 g, 0.277 mmol) was dissolved in DMF (2.8 mL). EDCI (0.64 g, 0.332 mmol) and DMAP (3.42 mg, 0.028 mmol) were then added and the reaction mixture was stirred at 60° C. for 20 minutes. Methyl 3-(4-(S-methylsulfonimidoyl)-phenyl)propanoate (0.068 g, 0.277 mmol) was then added, and the reaction was allowed to stir for 3 hours at 60° C. The mixture was cooled to room temperature then taken up in EtOAc (10 mL) and extracted with brine (3×10 mL). The organic layer was dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude product was then purified over silica purified via column chromatography (gradient eluant mixture of MeOH in EtOAc: 0% to 10% MeOH) to give the title compound (0.060 g, 37%).

Workup

  1. stirringto stir for 3 hours at 60° C
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with brine (3×10 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4(s)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was then purified over silica
  8. custompurified via column chromatography (gradient eluant mixture of MeOH in EtOAc: 0% to 10% MeOH)

Sources & evidence

ORD record
ord-0cf63cbb99a442bf8788a371a5378c85
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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