Water → HCID 10238979, compound

HRID 1814881Notes

Reaction equation

HRID 1814881 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[S:40][CH:41]=[CH:42][N: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[S:40][CH:41]=[CH:42][N: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 10126210N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamideHCID 22498780HCID 22498780, compound

Product 1

HCID 10238979HCID 10238979, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Diisopropylethylamine (0.24 mL) and N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 2, 0.250 g) were added to a solution of rac-2-(methylamino)-1-(1,3-thiazol-2-yl)ethanol (Preparation 53, 0.217 g) in DMF (15 mL). The reaction mixture was heated to 90° C. for 2 h. The mixture was allowed to cool to room temperature, poured into water (30 mL), and was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 98/2, 95/5) followed by recrystallization from ethyl acetate to yield 0.120 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 114-116° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.55, 7.70, 7.61, 7.41-7.32, 6.86, 6.13, 5.034.98, 4.55, 3.91, 3.77, 2.89-2.84, 2.74-2.69, 2.35; MS (ESI+) m/z 487 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. extractionwas extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was purified by column chromatography (CH2Cl2/methanol; 98/2, 95/5)
  8. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-674b36c74cf042d3befe65eb1a2408a5
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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