3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-amine → 6-chloro-2-fluoro-N-(3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide

HRID 1943940Notes

Reaction equation

HRID 1943940 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([NH2:14])[CH:12]=2)[NH:7][N:6]=1.[Cl:15][C:16]1[C:21]([C:22](O)=[O:23])=[C:20]([F:25])[C:19]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])=[CH:18][CH:17]=1>>[Cl:15][C:16]1[C:21]([C:22]([NH:14][C:11]2[CH:12]=[C:13]3[C:5]([O:4][CH2:3][CH2:2][F:1])=[N:6][NH:7][C:8]3=[N:9][CH:10]=2)=[O:23])=[C:20]([F:25])[C:19]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 442237483-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-amineHCID 580875006-Chloro-2-fluoro-3-(propane-1-sulfonamido)benzoic acid

Product 1

HCID 866525076-chloro-2-fluoro-N-(3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide

Procedure

6-Chloro-2-fluoro-N-(3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide was prepared according to the general procedure of Example 78, Step D, using 3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-amine (0.035 g, 0.18 mmol) and 6-chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (0.058 g, 0.20 mmol). The crude material was purified by silica gel flash column chromatography (5 to 7% 7N NH3-MeOH in CH2Cl2) to afford the desired product which was triturated with Et2O (51 mg, 60% yield). LRMS (ACPI pos) m/e 474.0 (M+1). 1H NMR (400 MHz, d6-DMSO) δ 12.68 (s, 1H), 11.10 (s, 1H), 9.99 (br s, 1H), 8.58 (d, 1H), 8.54 (d, 1H), 7.55 (t, 1H), 7.46 (d, 1H), 4.91 (m, 1H), 4.78 (m, 1H), 4.63 (m, 1H), 4.55 (m, 1H), 3.16 (t, 2H), 1.75 (m, 2H), 0.99 (t, 3H); 19F NMR (376 MHz, DMSO) δ−124.0, −223.1.

Workup

  1. custom6-Chloro-2-fluoro-N-(3-(2-fluoroethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide was prepared
  2. customThe crude material was purified by silica gel flash column chromatography (5 to 7% 7N NH3-MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5fc48a5ad8ec44f0aa69ad31f4239634
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

Loading…