Sodium Chloride → HCID 10152976, compound

HRID 1814887Notes

Reaction equation

HRID 1814887 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:27])[C:12]3[CH:19]=[C:18]([CH2:20][NH:21][CH2:22][CH:23]([OH:26])[CH2:24]Cl)[O:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[SH:38].[CH:39](N(C(C)C)CC)(C)C.[Na+].[Cl-]>CCO>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:27])[C:12]3[CH:19]=[C:18]([CH2:20][N:21]([CH2:22][CH:23]([OH:26])[CH2:24][S:38][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[O:31][CH3:30])[CH3:39])[O:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 23642ThioguaiacolHCID 81531DiisopropylethylamineHCID 22498722HCID 22498722, compound

Product 1

HCID 10152976HCID 10152976, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-2-(((3-chloro-2-hydroxypropyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 63, 0.181 g), 2-methoxythiophenol (0.058 mL), and diisopropylethylamine (0.097 mL) in absolute EtOH (16 mL) was heated to reflux overnight. The reaction was poured into 50% saturated aqueous NaCl (50 mL) and extracted with CHCl3. The combined organic layers were dried and concentrated. The crude product was purified by column chromatography (acetone/CHCl3/NH4OH; 1/2/0.5%) and triturated with Et2O/hexanes. The resulting solid was collected and dried overnight to yield 0.10 g of the title compound as a white solid. Physical characteristics. M.p. 145-147° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.66, 8.52, 7.40, 7.34, 7.22, 7.13, 6.89, 4.96, 4.55, 3.84-3.64, 3.02, 2.84, 2.55, 2.44, 2.29; 13C NMR (DMSO-d6) δ 174.1, 165.7, 157.4, 154.5, 152.7, 143.1, 140.0, 132.8, 130.5, 129.8, 128.1, 127.4, 126.8, 122.3, 116.6, 115.2, 112.0, 107.2, 68.8, 62.1, 56.9, 55.0, 44.3, 42.7, 38.8, 37.5. Anal. Found: C, 60.38; H, 5.56; N, 7.45.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. extractionextracted with CHCl3
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (acetone/CHCl3/NH4OH; 1/2/0.5%)
  7. customtriturated with Et2O/hexanes
  8. customThe resulting solid was collected
  9. customdried overnight

Sources & evidence

ORD record
ord-c8027a0ec30c45f8b6a2987bd9cc566e
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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