Pyridine → HCID 46873758, compound

HRID 2272820Notes

Reaction equation

HRID 2272820 reaction equation
[C:1](N)(=O)[C:2]1[CH:7]=CC=C[CH:3]=1.[CH3:10][C:11]1[C:12]([O:35][CH:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)=[CH:13][CH:14]=[C:15]2[C:20]=1[O:19][C:18](=[O:21])[C:17]([NH:22][C:23](=[O:34])C(OCC1C=CC=CC=1)=O)=[CH:16]2.CO[C:45]1[CH:46]=[C:47](OCOC)[C:48]([CH3:55])=[C:49]([O:51][CH2:52][O:53]C)[CH:50]=1.N1C=CC=C[CH:61]=1>[Pd].C1COCC1>[C:52]([O:51][C:49]1[CH:50]=[CH:45][C:46]([C:23](=[O:34])[NH:22][C:17]2[C:18](=[O:21])[O:19][C:20]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[C:12]([O:35][CH:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)[C:11]=3[CH3:10])=[CH:47][C:48]=1[CH2:55][CH:1]=[C:2]([CH3:7])[CH3:3])(=[O:53])[CH3:61]

Participants

7

Reactant 4

HCID 1049PyridineHCID 2331BenzamideHCID 251387855-Methoxy-1,3-bis(methoxymethoxy)-2-methylbenzeneHCID 86652366HCID 86652366, compound

Product 1

HCID 46873758HCID 46873758, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

General procedure III for the Preparation of benzamide 29a-g: Palladium on carbon (10%, 10 mg) was added to a solution of 28a (85 mg, 0.2 mmol) in THF. The suspension was stirred overnight under a hydrogen atmosphere before it was filtered. The filtrate was concentrated and dried under vacuum for 4 hours before it was redissolved in THF (5 mL). To it was added freshly prepared acid chloride 9 (80 mg, 0.3 mmol) in THF (5 mL) and dry pyridine (32 mg, 0.4 mmol). The resulting mixture was stirred at room temperature overnight and concentrated to dryness. The residue was purified by column chromatography on silica using methylene chloride and methanol (10:1) as eluent to afford 29a as white amorphous solid (76 mg, 73%). 1H NMR (500 MHz, CDCl3), δ 8.79 (s, 1H), 8.71 (s, 1H), 7.81 (d, J=2.1, 1H), 7.77 (dd, J=8.3, 2.1, 1H), 7.34 (d, J=8.6, 1H), 7.18 (d, J=8.3, 1H), 6.89 (d, J=8.6, 1H), 5.25 (m, 1H), 4.52 (m, 1H), 3.33 (d, J=7.2, 2H), 2.76˜2.70 (m, 2H), 2.55˜2.45 (m, 2H), 2.40 (s, 3H), 2.35 (s, 6H), 2.15˜2.09 (m, 2H), 1.97˜1.92 (m, 2H), 1.78 (s, 3H), 1.74 (s, 3H). 13C NMR δ (125 MHz, CDCl3) 169.1, 165.6, 159.6, 157.1, 152.3, 149.7, 134.8, 134.5, 131.8, 129.5, 126.1, 125.8, 124.8, 123.1, 121.7, 120.8, 115.4, 113.5, 110.6, 77.4, 52.3, 46.2, 30.5, 29.0, 25.9, 21.1, 18.1, 8.6. IR (film) νmax 3400, 2922, 2851, 1765, 1711, 1672, 1607, 1526, 1493, 1369, 1248, 1202, 1175, 1099, 1040 cm−1. HRMS (ESI+) m/z Calc for [M+H+] C30H35N2O6 519.2495. found: 519.2485.

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated
  3. customdried under vacuum for 4 hours before it
  4. dissolutionwas redissolved in THF (5 mL)
  5. stirringThe resulting mixture was stirred at room temperature overnight
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-ad3a56bd6653486e817bebbd364d87d9
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

Loading…