Water → HCID 10288846, compound

HRID 1814873Notes

Reaction equation

HRID 1814873 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([OH:18])[CH3:17].[Cl:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][NH:25][C:26]([C:28]2[C:29](=[O:40])[C:30]3[CH:37]=[C:36]([CH2:38]Cl)[O:35][C:31]=3[N:32]([CH3:34])[CH:33]=2)=[O:27])=[CH:22][CH:21]=1.O>CN(C=O)C>[Cl:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][NH:25][C:26]([C:28]2[C:29](=[O:40])[C:30]3[CH:37]=[C:36]([CH2:38][N:4]([CH2:17][CH:16]([OH:18])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=4)[CH3:1])[O:35][C:31]=3[N:32]([CH3:34])[CH:33]=2)=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 86784alpha-Methyl-2-pyridinemethanolHCID 10126210N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

Product 1

HCID 10288846HCID 10288846, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Diisopropylethylamine (0.11 mL) and rac-2-methylamino)-1-pyridin-2-ylethanol (Preparation 36, 0.094 g) were added to a suspension of N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamide (Example 2, 0.150 g) in DMF (10 mL). The reaction mixture was heated to 90° C. for 1 h. The mixture was allowed to cool to room temperature, poured into water (25 mL), and was extracted with CH2Cl2 (4×25 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2, 97/3, 95/5) followed by recrystallization from ethyl acetate to yield 0.082 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 130-132° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.54, 8.43-8.42, 7.76-7.73, 7.47-7.45, 7.41-7.32, 7.24-7.21, 6.83, 5.31, 4.79-4.74, 4.55, 3.89, 3.74, 2.79-2.74, 2.66-2.61, 2.33; MS (ESI+) m/z 481 (M+H)+. Anal. Found: C, 62.08; H, 5.25; N, 11.57; Cl, 7.39.

Workup

  1. temperatureto cool to room temperature
  2. extractionwas extracted with CH2Cl2 (4×25 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; 99/1, 98/2, 97/3, 95/5)
  7. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-75ed03ae0b954d32944e528cfc064884
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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