2-Phenoxybenzoic acid → N-(3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-phenoxybenzamide

HRID 1676340Notes

Reaction equation

HRID 1676340 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.[O:29]([C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38](O)=[O:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[F:1][C:2]1[CH:3]=[C:4]([NH:28][C:38](=[O:39])[C:37]2[CH:41]=[CH:42][CH:43]=[CH:44][C:36]=2[O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[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 752372-Phenoxybenzoic acidHCID 673454993-Fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)aniline

Product 1

HCID 58949497N-(3-fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-phenoxybenzamideYield 67%

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 2-phenoxybenzoic acid according to the procedure of Example 89. The crude was purified by silica gel flash column chromatography (10% MeOH in CH2Cl2) to afford 25 mg (67%) of the desired product. LRMS (ESI pos) m/e 593.3 (M+1). 1H-NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 8.48 (d, 1H), 8.36 (d, 1H), 7.87 (dd, 1H), 7.58 (s, 1H), 7.46 (t, 3H), 7.29 (m, 3H), 7.21 (d, 1H), 7.17 (m, 2H), 6.91 (d, 1H), 6.51 (dd, 1H), 3.60 (s, 2H), 2.52-2.71 (m, 8H), 2.32 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −126.7.

Workup

  1. customThe crude was purified by silica gel flash column chromatography (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0de014842c54446fad643bbf98f0c991
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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