3-Fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)aniline → N-(3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-(4-fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxamide

HRID 1676322Notes

Reaction equation

HRID 1676322 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]#[C:19][CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[S:17][C:10]=12.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:40][CH2:39][C:38]([CH3:44])([C:41](O)=[O:42])[C:37]2=[O:45])=[CH:32][CH:31]=1>>[F:1][C:2]1[CH:3]=[C:4]([NH:28][C:41]([C:38]2([CH3:44])[CH2:39][CH2:40][N:36]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)[C:37]2=[O:45])=[O:42])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]#[C:19][CH2:20][N:21]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]3)[S:17][C:10]=12

Participants

3

Reactant 2

HCID 673454993-Fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)anilineHCID 673473951-(4-Fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 58949500N-(3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-(4-fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxamideYield 84%

Procedure

Prepared from 3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)aniline (Example 17, Step B) and 1-(4-fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxylic acid according to the procedure of Example 89. The crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2) to afford 26 mg (84%) of the desired product. The crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2) to afford 66 mg (62%) of the desired product. LRMS (APCI pos) m/e 616.1 (M+1). 1H-NMR (400 MHz, CD3OD) δ 8.49 (d, 1H), 7.87 (dd, 1H), 7.68 (m, 2H), 7.59 (s, 1H), 7.45 (m, 1H), 7.36 (t, 1H), 7.15 (t, 2H), 6.69 (d, 1H), 4.25 (t, 2H), 3.91 (m, 2H), 3.68 (s, 2H), 2.79 (m, 6H), 2.56 (m, 2H), 2.30 (s, 3H), 2.18 (m, 2H), 1.66 (s, 3H); 19F NMR (376 MHz, CD3OD) δ −119.0, −130.0.

Workup

  1. customThe crude was purified by silica gel flash column chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4247f153f7d548be8673daeb2481651e
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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