Water → HCID 10238911, compound

HRID 1814879Notes

Reaction equation

HRID 1814879 reaction equation
C(N(CC)C(C)C)(C)C.[Cl:10][C:11]1[CH:33]=[CH:32][C:14]([CH2:15][NH:16][C:17]([C:19]2[C:20](=[O:31])[C:21]3[CH:28]=[C:27]([CH2:29]Cl)[O:26][C:22]=3[N:23]([CH3:25])[CH:24]=2)=[O:18])=[CH:13][CH:12]=1.[CH3:34][NH:35][CH2:36][CH:37]([C:39]1[N:40]([CH3:44])[CH:41]=[CH:42][CH:43]=1)[OH:38].O>CN(C=O)C>[Cl:10][C:11]1[CH:33]=[CH:32][C:14]([CH2:15][NH:16][C:17]([C:19]2[C:20](=[O:31])[C:21]3[CH:28]=[C:27]([CH2:29][N:35]([CH2:36][CH:37]([OH:38])[C:39]4[N:40]([CH3:44])[CH:41]=[CH:42][CH:43]=4)[CH3:34])[O:26][C:22]=3[N:23]([CH3:25])[CH:24]=2)=[O:18])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 10125080HCID 10125080, compoundHCID 10126210N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

Product 1

HCID 10238911HCID 10238911, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Diisopropylethylamine (0.14 mL) and N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 2, 0.150 g) were added to a solution of rac-2-(methylamino)-1-(1-methyl-1H-pyrrol-2-yl)ethanol (Preparation 48, 0.126 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 oil was purified by column chromatography (CH2Cl2/methanol, 98/2) followed by recrystallization from ethyl acetate to yield 0.126 g the title compound as a white solid. Physical characteristics. M.p. 122-124° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.55, 7.41-7.32, 6.89, 6.61-6.60, 5.85-5.83, 4.84, 4.74-4.69, 4.55, 3.91, 3.79-3.71, 3.58, 2.79-2.70, 2.31; 13C NMR (100 MHz, CDCl3) δ 173.7, 164.7, 153.2, 150.6, 141.1, 137.3, 132.8, 131.4, 128.9, 128.6, 123.4, 116.8, 114.8, 106.8, 106.6, 106.0, 61.9, 60.8, 54.3, 42.5, 41.9, 37.8, 34.1; MS (ESI+) m/z 483 (M+H)+.

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 oil was purified by column chromatography (CH2Cl2/methanol, 98/2)
  7. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-33eda1827e7e4792af0815ab56bd0b99
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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