N,N-Diethylaniline → HCID 58913113, compound

HRID 1296694Notes

Reaction equation

HRID 1296694 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:29][CH:28]=3)=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)C=C.CCN([C:46]1[CH:47]=CC=C[CH:51]=1)CC>>[OH:4][C:5]1[C:14]([CH2:47][CH:46]=[CH2:51])=[C:13]2[C:8]([C:9]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:31][CH:32]=3)=[C:10]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:20][CH:21]=3)[C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 7061N,N-DiethylanilineHCID 86598942HCID 86598942, compound

Product 1

HCID 58913113HCID 58913113, compoundYield 18%

Conditions

Temperature
190 °C

Procedure

7-Prop-2-enyloxy-4-{(4-(2-pyrrolidinylethoxy)phenyl)methyl}-3-(4-(trifluoromethyl) Phenyl)-2H-chromen-2-one (0.150 g.) was dissolved in diethylaniline (4 mL) and allowed to stir at 190° C. for two hours. The resultant solution was extracted with methylene chloride (3×) and 1M hydrochloric acid. The organic layers were dried over sodium sulfate and filtered, and the solvent was removed under reduced pressure to afford a crude brown solid. The solid was purified via preparative-HPLC (40–100% acetonitrile/water, 20 mL/min.) to afford the title compound (0.027 g, 18% yield). 1H-NMR (CDCl3) δ 7.63 (d, 2H), 7.38 (d, 2H), 7.25 (d, 1H), 6.92 (d, 2H), 6.75 (d, 2H), 6.70 (d, 1H), 6.0 (m, 1H), 5.13 (dd, 2H), 4.12 (t, 2H), 3.94 (s, 2H), 3.66 (d, 2H), 3.05 (bs, 2H), 2.8 (bs, 4H), 1.25 (s, 2H). MS (m/z) 550 (M+1)+.

Workup

  1. extractionThe resultant solution was extracted with methylene chloride (3×) and 1M hydrochloric acid
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customto afford a crude brown solid
  6. customThe solid was purified via preparative-HPLC (40–100% acetonitrile/water, 20 mL/min.)

Sources & evidence

ORD record
ord-8b82cb7354c84f809f1b6203d6da2086
Source dataset
uspto-grants-2007_07
Patent number
US07247646B2

Reaction notes

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