1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59852843, compound

HRID 2374027Notes

Reaction equation

HRID 2374027 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=[O:19])=[CH:13][CH:12]=1.C1C=CC2N(O)N=[N:34]C=2C=1.CCN=C=NCCCN(C)C>>[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH2:34])=[O:19])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59852970HCID 59852970, compound

Product 1

HCID 59852843HCID 59852843, compoundYield 66.1%

Procedure

A 25 mL round bottom flask was charged with 2-(4-(4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)phenyl)acetic acid (50 mg, 0.136 mmol), HOBT (46 mg, 0.34 mmol), and EDCI (65 mg, 0.34 mmol). The flask was flushed with nitrogen and then DMF was added (1 mL). After stirring at rt for 1 h, the solution was cooled to 0° C. and then charged with ammonium hydroxide (0.5 mL). The reaction was stirred at 0° C. for 1 h and was then diluted with brine (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (20% MeOH/EtOAc) to give the title compound (33 mg, 66%) as a colorless oil. 1H NMR (CD3OD) δ 8.49 (s, 1H), 8.38 (d, 1H, J=5.6 Hz), 8.10 (dd, 1H, J=10.4, 2.4 Hz), 7.99 (m, 1H), 7.45 (d, 2H, J=8.2 Hz), 7.30 (d, 2H, J=8.2 Hz), 7.28 (m, 1H), 6.93 (d, 1H, J=5.6 Hz), 3.44 (s, 2H); MS(ESI+) m/z 368.18 (M+H)+.

Workup

  1. customThe flask was flushed with nitrogen
  2. additionDMF was added (1 mL)
  3. temperaturethe solution was cooled to 0° C.
  4. additioncharged with ammonium hydroxide (0.5 mL)
  5. stirringThe reaction was stirred at 0° C. for 1 h
  6. additionwas then diluted with brine (5 mL)
  7. extractionextracted with ethyl acetate (3×5 mL)
  8. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash column chromatography on silica gel (20% MeOH/EtOAc)

Sources & evidence

ORD record
ord-e5ca24d5f3ea4d72918ff53f9dfbde24
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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