Diisopropylethylamine → HCID 59451502, compound

HRID 1874768Notes

Reaction equation

HRID 1874768 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:19])=[C:7]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([Cl:18])[CH:17]=2)[C:13]#[N:14])[CH:8]=1.[CH3:20][O:21][C:22]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25].CCN(C(C)C)C(C)C>C(#N)C>[Cl:19][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:22]=2[O:21][CH3:20])=[CH:8][C:7]=1[O:9][C:10]1[CH:11]=[C:12]([C:13]#[N:14])[CH:15]=[C:16]([Cl:18])[CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27347192,4-Dimethoxybenzoyl chlorideHCID 594514053-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 59451502HCID 59451502, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile (0.05 g, 0.17 mmol), 2,4-bis(methyloxy)benzoyl chloride (0.046 g, 0.25 mmol) and DIPEA (0.05 mL, 0.25 mmol) were dissolved in acetonitrile (3 mL) and stirred overnight. The solvent was evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were lyophilized then EtOAc (25 mL) and saturated NaHCO3 (10 mL) were added. The layers were separated and the aqueous layer extracted with EtOAc (2×10 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (0.045 g, 57%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.57 (t, 1H), 7.79 (s, 1H), 7.67-7.77 (m, 1H), 7.58 (d, 1H), 7.44 (s, 1H), 7.36 (s, 1H), 7.22-7.26 (m, 1H), 7.12-7.22 (m, 1H), 6.59 (d, 1H), 6.62 (s, 1H), 4.46 (d, 2H), 3.83 (s, 3H), 3.80 (s, 3H). MS: m/z 457.0 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customPurification
  3. additionEtOAc (25 mL) and saturated NaHCO3 (10 mL) were added
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with EtOAc (2×10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-805246c76c174fc3a04d31530600b2ee
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…