1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 89906862, compound

HRID 525746Notes

Reaction equation

HRID 525746 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[CH2:13]([O:15][C:16]([C:18]1[C:19]([Cl:27])=[N:20][CH:21]=[C:22]([C:24](O)=[O:25])[CH:23]=1)=[O:17])[CH3:14].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C=O)C.CCOC(C)=O>[CH2:13]([O:15][C:16](=[O:17])[C:18]1[CH:23]=[C:22]([C:24](=[O:25])[NH:8][C:7]2[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=2)[CH:21]=[N:20][C:19]=1[Cl:27])[CH3:14]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6008484-(Trifluoromethoxy)anilineHCID 89907005HCID 89907005, compound

Product 1

HCID 89906862HCID 89906862, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Trifluoromethoxyaniline (1.79 mL, 13.3 mmol) was added to a stirred solution of 2-chloropyridine-3,5-dicarboxylic acid ethyl ester (Stage 72.6, 3.20 g, 14 mmol), 1-hydroxybenzotriazole (3.20 g, 20.9 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.94 g, 15.3 mmol) in DMF (50 mL). The mixture was stirred for 2 h and then treated with EtOAc, washed with a sat. aq. solution of NaHCO3 and brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure and the crude product was purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc, from 0 to 50% EtOAc) and recrystallized from n-hexane/EtOAc to afford the title compound as a colorless crystalline solid. m.p. 135-137° C., HPLC (Condition 4) tR=6.59 min, UPLC-MS (Condition 8) tR=1.24 min, m/z=389.0 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.35 (t, J=7.23 Hz, 3H), 4.39 (q, J=7.04 Hz, 2H), 7.39 (d, J=8.60 Hz, 2H), 7.76-7.92 (m, 2H), 8.69 (d, J=2.35 Hz, 1H), 9.08 (d, J=2.35 Hz, 1H), 10.76 (s, 1H).

Workup

  1. washwashed with a sat. aq. solution of NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated off under reduced pressure
  4. customthe crude product was purified by flash chromatography (RediSep® Silica gel column, n-heptane/EtOAc, from 0 to 50% EtOAc)
  5. customrecrystallized from n-hexane/EtOAc

Sources & evidence

ORD record
ord-8954a2bc64a549bda0e9ea41ed8c64ed
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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