Veratric Acid → HCID 16731289, compound

HRID 507340Notes

Reaction equation

HRID 507340 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:44]1[C:56]2[NH:55][C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48]=2[C:47]([O:57][CH2:58][CH:59]([OH:63])[CH2:60][NH:61][CH3:62])=[CH:46][CH:45]=1>CN(C=O)C.C(Cl)Cl>[CH:44]1[C:56]2[NH:55][C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48]=2[C:47]([O:57][CH2:58][CH:59]([OH:63])[CH2:60][N:61]([CH3:62])[C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:46][CH:45]=1

Participants

8

Reactant 5

HCID 7121Veratric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 58878128HCID 58878128, compound

Product 1

HCID 16731289HCID 16731289, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,4-Dimethoxybenzoic acid (0.2 g, 1.11 mmol) in DMF (5 mL) was added DIPEA (0.48 mL, 2.8 mmol), EDCI (0.355 g, 1.85 mmol), HOBt (0.05 g, 0.37 mmol) followed by 1-(9H-carbazol-4-yloxy)-3-(methylamino)propan-2-ol (0.25 g, 0.925 mmol) prepared following the procedure described above in step I, example 72. The reaction was stirred at room temperature for 12 hours and was diluted with DCM (50 mL), washed with water and brine solution. The organic layer was dried over anhydrous Na2SO4, concentrated. The crude compound was purified by dissolution in dichloromethane (3 mL) and precipitation by adding diisopropyl ether (5 mL) and hexane (10 mL). The resulting white solid was filtered, and dried to afford the desired compound (0.15 g, 38%) with m.p.: 77-80° C. 1H NMR (400 MHz, CDCl3) δ (ppm): 3.10-3.40 (m, 3H), 3.70-4.10 (m, 7H), 4.07 (s, 1H), 4.20-4.25 (m, 1H), 4.38 (s, 1H), 4.56 (s, 1H), 4.76 (s, 1H), 6.74 (s, 1H), 6.87 (s, 1H), 6.90-7.15 (m, 4H), 7.20-7.49 (m, 3H), 8.17 (s, 1H), 8.30 (s, 1H). MS m/z: 435.0 (M+).

Workup

  1. customprepared
  2. washwashed with water and brine solution
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude compound was purified by dissolution in dichloromethane (3 mL)
  6. customprecipitation
  7. additionby adding diisopropyl ether (5 mL) and hexane (10 mL)
  8. filtrationThe resulting white solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-a9857f2c776646e6bb6f57dcf840e26b
Source dataset
uspto-grants-2010_08
Patent number
US07786142B2

Reaction notes

Loading…