5-(5-(benzyloxy)-6-(3-(hydroxymethyl)pyrazolo[1,5-a]pyridin-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide → 2-(4-fluorophenyl)-5-(5-hydroxy-6-(3-(hydroxymethyl)pyrazolo[1,5-a]pyridin-2-yl)pyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 1776901Notes

Reaction equation

HRID 1776901 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:26]2[C:27]([N:46]([CH3:51])[S:47]([CH3:50])(=[O:49])=[O:48])=[CH:28][C:29]3[O:33][C:32]([C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)=[C:31]([C:41]([NH:43][CH3:44])=[O:42])[C:30]=3[CH:45]=2)=[N:13][C:14]=1[C:15]1[C:23]([CH2:24][OH:25])=[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][N:17]2[N:16]=1)C1C=CC=CC=1>CO.[Pd]>[F:40][C:37]1[CH:36]=[CH:35][C:34]([C:32]2[O:33][C:29]3[CH:28]=[C:27]([N:46]([CH3:51])[S:47]([CH3:50])(=[O:48])=[O:49])[C:26]([C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[C:14]([C:15]5[C:23]([CH2:24][OH:25])=[C:18]6[CH:19]=[CH:20][CH:21]=[CH:22][N:17]6[N:16]=5)[N:13]=4)=[CH:45][C:30]=3[C:31]=2[C:41]([NH:43][CH3:44])=[O:42])=[CH:39][CH:38]=1

Participants

4

Reactant 1

HCID 712954825-(5-(benzyloxy)-6-(3-(hydroxymethyl)pyrazolo[1,5-a]pyridin-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 1363413672-(4-fluorophenyl)-5-(5-hydroxy-6-(3-(hydroxymethyl)pyrazolo[1,5-a]pyridin-2-yl)pyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 46.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound 5-(5-(benzyloxy)-6-(3-(hydroxymethyl)pyrazolo[1,5-a]pyridin-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (250 mg, 0.35 mmol) and Pd/C (20 mg) in MeOH (2 mL) was stirred at room temperature under H2 for 2 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified using prep-TLC (EA:MeOH=20:1) to provide the product of compound 2-(4-fluorophenyl)-5-(5-hydroxy-6-(3-(hydroxymethyl)pyrazolo[1,5-a]pyridin-2-yl)pyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 mg, yield: 46%). 1H-NMR (Methanol-d4, 400 MHz) δ 8.50 (d, J=6.8 Hz, 1H), 7.98 (dd, J=5.2, 8.4 Hz, 2H), 7.84 (s, 2H), 7.78 (d, J=9.2 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.45 (d, J=8.4 Hz, 1H), 7.29˜7.23 (m, 3H), 6.93 (t, J=6.8 Hz, 1H), 4.77 (s, 2H), 3.26 (s, 3H), 2.93 (s, 3H), 2.90 (s, 3H). MS (M+H)+: 616.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was purified

Sources & evidence

ORD record
ord-6d96f53fae6843b68ef6927aa4ef3a6c
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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