Acetonitrile → HCID 46184988, compound

HRID 1895860Notes

Reaction equation

HRID 1895860 reaction equation
COC1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[C:12]([NH2:13])=[C:11]([C:14]3[C:18](=[NH:19])[N:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH2:28]C)=[CH:23][CH:22]=4)[C:16](=[O:30])[N:15]=3)[N:10]=[CH:9]2)=[CH:5]C=1.[CH:33]([O:40][CH2:41][CH3:42])(OCC)OCC.[CH3:43]C#N>S(=O)(=O)(O)O>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:17]2[C:18]3=[N:19][CH:43]=[N:13][C:12]4[N:8]([CH2:7][C:6]5[CH:5]=[CH:42][C:41]([O:40][CH3:33])=[CH:32][CH:31]=5)[CH:9]=[N:10][C:11]=4[C:14]3=[N:15][C:16]2=[O:30])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 31214Ethyl orthoformateHCID 66989017HCID 66989017, compound

Product 1

HCID 46184988HCID 46184988, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a suspension of 9 (1.0 g, 2.39 mmol, 1 equiv) in MeCN (10 mL), triethyl orthoformate (2.8 g, 19.13 mmol, 8 equiv) was added followed by 2 drops of sulfuric acid. The reaction mixture was heated at reflux for 1.5 h until starting material was disappeared (TLC). The precipitated product was filtered, washed with diethyl ether and dried under vacuum to afford 3 as pale yellow solid (0.77 g, 76%). mp: 175-177° C., IR: 1737 (C═O), 1610, 1589, 1251, 1176 cm−1. 1H NMR (400 MHz, d6-DMSO): δ=3.69 (s, 3H, OCH3), 3.70 (s, 3H, OCH3), 5.08 (s, 2H, CH2), 5.51 (s, 2H, CH2), 6.85 (d, J=8.2 Hz, 2H, Ar—H), 6.89 (d, J=8.2 Hz, 2H, Ar—H), 7.29 (d, J=8.2 Hz, 2H, Ar—H), 7.33 (d, J=8.2 Hz, 2H, Ar—H), 8.75 (s, 1H, Ar—C═N—H), 8.92 (s, 1H, Imid-H). 13C NMR (100 MHz, d6-DMSO): δ=43.4, 47.0, 55.6, 55.7, 114.4, 114.6, 128.5, 128.8, 129.2, 129.7, 129.8, 148.9, 150.3, 156.3, 159.2, 159.5, 160.2, 166.3. HRMS (FAB) Calcd for C23H20N6O3, 428.1597 (M+); observed m/z 429.1667 (M+H)+.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1.5 h
  4. filtrationThe precipitated product was filtered
  5. washwashed with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-6a85e6b36eea4f5e88b23e61599d5332
Source dataset
uspto-grants-2013_08
Patent number
US08518901B2

Reaction notes

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