Water → N-(4-Chlorobenzyl)-2-(((2-hydroxy-2-phenylethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

HRID 1814870Notes

Reaction equation

[CH:1]([N:4]([CH2:8][CH3:9])[CH:5]([CH3:7])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(CCl)[O:26][C:22]=3[N:23]([CH3:25])[CH:24]=2)=[O:18])=[CH:13][CH:12]=1.[OH2:34]>CN(C=O)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH:16][C:17]([C:19]2[C:20](=[O:31])[C:21]3[CH:28]=[C:9]([CH2:8][N:4]([CH2:5][CH:7]([OH:34])[C:11]4[CH:33]=[CH:32][CH:14]=[CH:13][CH:12]=4)[CH3:1])[O:26][C:22]=3[N:23]([CH3:25])[CH:24]=2)=[O:18])=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 90 °C

Procedure

N,N-Diisopropylethylamine (0.111 mL) and (x-(methylaminomethyl)-benzyl alcohol (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 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 0.095 g of the title compound as a pale yellow solid. Physical characteristics. M.p. 118-121° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.54, 7.41-7.35, 7.32-7.25, 7.22-7.18, 6.84, 5.10, 4.734.69, 4.55, 3.89, 3.73, 2.62-2.54, 2.32; MS (ESI+) m/z 480 (M+H)+. Anal. Found: C, 63.48; H, 5.56; N, 8.24; Cl, 6.94.

Workup

temperatureto cool to room temperature
filtrationThe suspension was filtered
customthe resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2)
customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record: ord-2dbcba68eb9243dd93a5d7029c9bd85b
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878705B2

Reaction notes

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