HCID 66767137, compound → HCID 58949426, compound

HRID 1676314Notes

Reaction equation

HRID 1676314 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[C:41](=[O:42])[C:40]([C:43](O)=[O:44])=[CH:39][C:38]([CH3:46])=[N:37]2)=[CH:32][CH:31]=1>>[F:1][C:2]1[CH:3]=[C:4]([NH:28][C:43]([C:40]2[C:41](=[O:42])[N:36]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)[N:37]=[C:38]([CH3:46])[CH:39]=2)=[O:44])[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 66767137HCID 66767137, compoundHCID 673454993-Fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)aniline

Product 1

HCID 58949426HCID 58949426, compoundYield 14%

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-(4-fluorophenyl)-6-methyl-3-oxo-2,3-dihydropyridazine-4-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 4.5 mg (14%) of the desired product. LRMS (ESI pos) m/e 627.3 (M+1). 1H-NMR (400 MHz, CDCl3/CD3OD) δ 8.47 (d, 1H), 8.32 (s, 1H), 8.0 (dd, 1H), 7.62 (m, 3H), 7.45 (d, 1H), 7.34 (t, 1H), 7.27 (t, 2H), 6.65 (d, 1H), 3.66 (s, 2H), 2.77 (m, 8H), 2.56 (s, 3H), 2.34 (s, 3H); 19F NMR (376 MHz, CDCl3/CD3OD) δ −113.2, −127.6.

Workup

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

Sources & evidence

ORD record
ord-fa21a07f381e448f813d765d021e08f6
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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