Cesium carbonate → N-{1-[6-(5-Methyl-thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-ylmethyl]-piperidin-4-yl}-acetamide formate

HRID 1947540Notes

Reaction equation

HRID 1947540 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH2:9][N:10]3[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:19])[CH3:18])[CH2:12][CH2:11]3)=[CH:7][O:8][C:4]=2[CH:3]=1.[C:22]([O-])([O-:24])=[O:23].[Cs+].[Cs+].Cl[C:29]1[S:30][C:31]2[C:32]([N:38]=1)=[N:33][C:34]([CH3:37])=[CH:35][CH:36]=2>CN(C=O)C>[CH:22]([OH:24])=[O:23].[CH3:37][C:34]1[N:33]=[C:32]2[N:38]=[C:29]([O:1][C:2]3[CH:21]=[CH:20][C:5]4[C:6]([CH2:9][N:10]5[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:19])[CH3:18])[CH2:12][CH2:11]5)=[CH:7][O:8][C:4]=4[CH:3]=3)[S:30][C:31]2=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 189844612-Chloro-5-methyl-thiazolo[4,5-b]pyridineHCID 59577711N-[1-(6-Hydroxy-benzofuran-3-ylmethyl)-piperidin-4-yl]-acetamide

Product 1

HCID 68771565N-{1-[6-(5-Methyl-thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-ylmethyl]-piperidin-4-yl}-acetamide formateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-[1-(6-hydroxy-benzofuran-3-ylmethyl)-piperidin-4-yl]-acetamide (50 mg, 0.17 mmol), Cs2CO3 (170 mg, 0.52 mmol) in DMF (1.73 mL) was added 2-chloro-5-methyl-thiazolo[4,5-b]pyridine (40 mg, 0.22 mmol) and the reaction mixture was stirred (rt, 16 h). The reaction mixture was filtered and purified via reverse-phase preparative HPLC to provide the title compound as a white solid (67 mg, 79%). MS (ESI): mass calcd. for C23H24N4O3S, 436.16; m/z found, 437.0 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.91 (d, J=8.1, 1H), 7.83 (5, 1H), 7.71 (d, J=8.3, 1H), 7.63 (5, 1H), 7.32 (d, J=7.9, 1H), 7.09 (d, J=8.1, 1H), 5.77 (5, 1H), 3.93 (5, 3H), 3.17 (5, 2H), 2.61 (5, 3H), 2.47 (5, 2H), 1.97 (5, 5H), 1.78 (5, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified via reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-a167cc105ecf4e9f944e26a55253df07
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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