Water → HCID 10174262, compound

HRID 1814877Notes

Reaction equation

HRID 1814877 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][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[S:40][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 10126210N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamideHCID 22498745α-[(Methylamino)methyl]-2-thiophenemethanol

Product 1

HCID 10174262HCID 10174262, compoundYield 62.6%

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-thien-2-ylethanol (Preparation 46, 0.130 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; 99/1, 98/2) followed by recrystallization from ethyl acetate to yield 0.125 g of the title compound as a white solid. Physical characteristics. M.p. 145-147° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.54, 7.41-7.32, 6.97-6.93, 6.87, 6.42, 5.52, 4.984.93, 4.55, 3.91, 3.76, 2.70-2.60, 2.30; 13C NMR (100 MHz, CDCl3) δ 168.9, 159.9, 148.3, 145.6, 140.3, 136.2, 132.4, 127.9, 124.1, 123.8, 121.8, 119.8, 119.0, 112.0, 109.9, 101.8, 61.3, 59.6, 49.2, 37.7, 37.0, 32.9; MS (ESI+) m/z 486 (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; 99/1, 98/2)
  4. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e58cb1036516492dadd283ce7db141a4
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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