Formaldehyde → HCID 10173268, compound

HRID 1814868Notes

Reaction equation

HRID 1814868 reaction equation
C=O.[C:3](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:17][C:18]1[CH:44]=[CH:43][C:21]([CH2:22][NH:23][C:24]([C:26]2[C:27](=[O:42])[C:28]3[CH:35]=[C:34]([CH2:36][NH:37][CH2:38][CH:39]([OH:41])[CH3:40])[O:33][C:29]=3[N:30]([CH3:32])[CH:31]=2)=[O:25])=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>C(Cl)CCl>[Cl:17][C:18]1[CH:44]=[CH:43][C:21]([CH2:22][NH:23][C:24]([C:26]2[C:27](=[O:42])[C:28]3[CH:35]=[C:34]([CH2:36][N:37]([CH2:38][CH:39]([OH:41])[CH3:40])[CH3:3])[O:33][C:29]=3[N:30]([CH3:32])[CH:31]=2)=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22498748HCID 22498748, compound

Product 1

HCID 10173268HCID 10173268, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Aq. formaldehyde (0.19 mL) and sodium triacetoxy borohydride (0.526 g) were added to a suspension of N-(4-chlorobenzyl)-2-(((2-hydroxypropyl)-amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 33, 0.500 g) in],2-dichloroethane (50 mL). The reaction mixture was stirred at room temperature for 18 h. A sat. aq. sodium bicarbonate solution (30 mL) was added. The aqueous layer was separated and extracted with CH2Cl2 (4×50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 97/3, 96/4) followed by recrystallization from ethyl acetate to yield 0.301 g of the title compound as a white solid. Physical characteristics. M.p. 152° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.55, 7.41-7.32, 6.87, 4.55, 4.35, 3.92, 3.80-3.73, 3.69, 2.36-2.31, 2.28-2.20, 1.04; MS (EST+) m/z 418 (M+H)+.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with CH2Cl2 (4×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol; 97/3, 96/4)
  7. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-1dcf35d2eae549d19ca991287261be72
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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