Sodium Chloride → HCID 10196476, compound

HRID 1814888Notes

Reaction equation

HRID 1814888 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.[NH2:30][C:31]1[S:35][C:34]([SH:36])=[N:33][N:32]=1.[CH:37](N(C(C)C)CC)(C)C.[Na+].[Cl-]>CCO>[NH2:30][C:31]1[S:35][C:34]([S:36][CH2:24][CH:23]([OH:26])[CH2:22][N:21]([CH2:20][C:18]2[O:17][C:13]3[N:14]([CH3:16])[CH:15]=[C:10]([C:8]([NH:7][CH2:6][C:5]4[CH:28]=[CH:29][C:2]([Cl:1])=[CH:3][CH:4]=4)=[O:9])[C:11](=[O:27])[C:12]=3[CH:19]=2)[CH3:37])=[N:33][N:32]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 22498722HCID 22498722, compoundHCID 178509208HCID 178509208, compound

Product 1

HCID 10196476HCID 10196476, 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), 5-amino-1,3,4-thiadiazole-2-thiol (0.064 g), and diisopropylethylamine (0.097 mL) in absolute EtOH (16 mL) was heated to reflux overnight. The reaction was poured into 50% saturated aqueous NaCl (40 mL) and extracted with CHCl3. The organic layer was dried and concentrated. The crude product was purified by column chromatography (CHCl3MeOH/NH4OH, 93/7/0.5%) and triturated with Et2O/hexanes. The resulting solid was collected and dried overnight to yield 0.087 g of the title compound as a white solid. Physical characteristics. M.p. 200-204° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.64, 8.54, 7.39, 7.33, 7.23, 6.88, 5.11, 4.54, 3.92, 3.70, 3.29, 3.04, 2.4, 2.28; 3C NMR (DMSO-d6) δ 172.7, 169.2, 164.3, 153.2, 151.2, 141.8, 138.6, 131.3, 129.1, 128.3, 115.2, 113.8, 105.9, 67.2, 60.6, 53.4, 42.6, 41.3, 37.5. Anal. Found: C, 50.41; H, 4.74; N, 15.06.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. extractionextracted with CHCl3
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (CHCl3MeOH/NH4OH, 93/7/0.5%)
  7. customtriturated with Et2O/hexanes
  8. customThe resulting solid was collected
  9. customdried overnight

Sources & evidence

ORD record
ord-b27b56aa88ab4627975c6b5814da9a4a
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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