Water → HCID 22498735, compound

HRID 1814875

Reaction equation

HRID 1814875 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.[O:34]1[CH:38]=[CH:37][C:36]([CH:39]([OH:43])[CH2:40][NH:41][CH3:42])=[CH:35]1.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:41]([CH2:40][CH:39]([C:36]4[CH:37]=[CH:38][O:34][CH:35]=4)[OH:43])[CH3:42])[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 102858031-(Furan-3-yl)-2-(methylamino)ethan-1-ol

Product 1

HCID 22498735HCID 22498735, compoundYield 52.8%

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-1-(3-furyl)-2-(methylamino)ethanol (Preparation 43, 0.116 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 and was poured into water (25 mL). The suspension was filtered and the resulting solid was purified by column chromatography (CH2Cl2/methanol, 98/2) followed by recrystallization from ethyl acetate to yield 0.102 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 93-97° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.55, 7.54-7.53, 7.41-7.32, 6.87, 6.42, 4.97, 4.694.65, 4.55, 3.91, 3.74, 2.63-2.53, 2.30; 13C NMR (100 MHz, CDCl3) δ 173.7, 164.7, 153.2, 150.6, 143.4, 141.1, 139.4, 137.3, 132.8, 128.9, 126.0, 116.8, 114.7, 108.3, 106.6, 102.1, 63.2, 62.7, 54.1, 42.6, 41.8, 37.8; MS (ESI+) m/z 470 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe suspension was filtered
  3. customthe resulting solid was purified by column chromatography (CH2Cl2/methanol, 98/2)
  4. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-49465c14959e4a39b5000f75073c7615
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Linked notes

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