1,2,3-Trimethoxybenzene → HCID 178490871, compound

HRID 1895861Notes

Reaction equation

HRID 1895861 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:14]3=[N:15][CH:16]=[N:17][C:18]4[N:22](CC5C=CC(OC)=CC=5)[CH:21]=[N:20][C:19]=4[C:13]3=[N:12][C:11]2=[O:32])=[CH:5][CH:4]=1.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[C:36]=1[O:43][CH3:44]>C(O)(C(F)(F)F)=O>[CH3:33][O:34][C:35]1[C:36]([O:43][CH3:44])=[C:37]([O:41][CH3:42])[CH:38]=[CH:39][C:40]=1[C:13]12[NH:12][C:11](=[O:32])[N:10]([CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:14]1=[N:15][CH:16]=[N:17][C:18]1[NH:22][CH:21]=[N:20][C:19]=12

Participants

4

Reactant 2

HCID 124621,2,3-TrimethoxybenzeneHCID 46184988HCID 46184988, compound

Product 1

HCID 178490871HCID 178490871, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 3 (0.43 g, 1 mmol) in 1,2,3-trimethoxybenzene (5 mL), TFA (10 mL, dropwsie) was added. The reaction mixture was heated at 60° C. for 3 h. TFA was evaporated on rotary evaporator after the disappearance of starting material (TLC) and excess of sodium bicarbonate was added. The reaction mixture was extracted with EtOAc (30×3 mL), washed with brine, dried (anhyd. Na2SO4) and adsorbed over silica and purified through column chromatography to afford 14 as yellowish white solid (0.38 g, 80%); mp: decomposed >225° C. IR: 1734 (C═O str.), 1620, 1514, 1247 (C—O str.) cm−1. 1H NMR (400 MHz, d6-DMSO): δ=3.52 (s, 3H, OCH3), 3.69 (s, 6H, OCH3), 4.60 (dd, J=15.1, 18.3 Hz, 2H, CH2), 5.80 (J=8.7 Hz, 1H, Ar—H), 6.50 (J=8.7 Hz, 1H, Ar—H), 6.85 (d, J=8.7 Hz, 2H, Ar—H), 7.22 (d, J=8.7 Hz, 2H, Ar—H), 7.50 (s, 1H, Ar—CH═N—), 7:85 (s, 1H, Imid-H), 9.40 (brs, 1H, D2O-exchangable NH). 13C NMR (100 MHz, d6-DMSO): δ=42.9, 55.6, 56.3, 60.7, 60.8, 63.4, 106.7, 114.2, 120.0, 122.0, 122.8, 129.1, 129.9, 134.9, 137.2, 142.0, 146.0, 152.6, 154.2, 154.7, 156.6, 159.1. HRMS (FAB) Calcd for C24H24N6O5, 476.1808 (M+); observed m/z 477.1875 (M+H)+.

Workup

  1. additionwas added
  2. customTFA was evaporated on rotary evaporator after the disappearance of starting material (TLC)
  3. additionexcess of sodium bicarbonate was added
  4. extractionThe reaction mixture was extracted with EtOAc (30×3 mL)
  5. washwashed with brine
  6. dry with materialdried (anhyd. Na2SO4)
  7. custompurified through column chromatography

Sources & evidence

ORD record
ord-e110dd60f53c4dcf975b75c329e1a5ff
Source dataset
uspto-grants-2013_08
Patent number
US08518901B2

Reaction notes

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