3-(5-((2-(Dimethylamino)ethyl)(methyl)amino)pyridin-2-ylamino)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one → 2-(3-(5-(5-((2-(Dimethylamino)ethyl)(methyl)amino)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-5-fluoro-2-(hydroxymethyl)phenyl)-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-1(2H)-one

HRID 1919090Notes

Reaction equation

HRID 1919090 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:17][CH2:16][C:15]3[C:18]4[CH2:24][CH2:23][CH2:22][CH2:21][C:19]=4[S:20][C:14]=3[C:13]2=[O:25])=[CH:10][C:9]([F:26])=[CH:8][C:7]=1Br)(=O)C.[CH3:28][N:29]([CH3:58])[CH2:30][CH2:31][N:32]([CH3:57])[C:33]1[CH:34]=[CH:35][C:36]([NH:39][C:40]2[C:41](=[O:56])[N:42]([CH3:55])[CH:43]=[C:44](B3OC(C)(C)C(C)(C)O3)[CH:45]=2)=[N:37][CH:38]=1>>[CH3:28][N:29]([CH3:58])[CH2:30][CH2:31][N:32]([CH3:57])[C:33]1[CH:34]=[CH:35][C:36]([NH:39][C:40]2[C:41](=[O:56])[N:42]([CH3:55])[CH:43]=[C:44]([C:7]3[C:6]([CH2:5][OH:4])=[C:11]([N:12]4[CH2:17][CH2:16][C:15]5[C:18]6[CH2:24][CH2:23][CH2:22][CH2:21][C:19]=6[S:20][C:14]=5[C:13]4=[O:25])[CH:10]=[C:9]([F:26])[CH:8]=3)[CH:45]=2)=[N:37][CH:38]=1

Participants

3

Reactant 2

HCID 580436803-(5-((2-(Dimethylamino)ethyl)(methyl)amino)pyridin-2-ylamino)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-oneHCID 580437562-Bromo-4-fluoro-6-(1-oxo-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-2(1H)-yl)benzyl Acetate

Product 1

HCID 670163622-(3-(5-(5-((2-(Dimethylamino)ethyl)(methyl)amino)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-5-fluoro-2-(hydroxymethyl)phenyl)-3,4,5,6,7,8-hexahydrobenzothieno[2,3-c]pyridin-1(2H)-oneYield 8%

Procedure

Following Example 270, reaction of 212a (550 mg, 1.20 mmol) and 270d (428 mg, 1.00 mmol) afforded a 8% yield (49 mg) of 286 as an off-white solid: mp 122-123° C.; 1H NMR (500 MHz, DMSO-d6) d 8.45 (d, 1H, J=2.0 Hz), 8.20 (s, 1H), 7.69 (d, 1H, J=2.4 Hz), 7.31 (m, 2H), 7.17 (m, 3H), 4.83 (t, 1H, J=4.6 Hz), 4.32 (d, 2H, J=4.3 Hz), 4.06 (m, 1H), 3.87 (m, 1H), 3.58 (s, 3H), 2.96 (m, 1H), 2.86 (m, 1H), 2.83 (s, 3H), 2.78 (m, 2H), 2.54 (m, 1H), 2.32 (t, 2H, J=7.0 Hz), 2.14 (s, 6H), 1.80 (m, 4H); MS (ESI+) m/z 631.3 (M+H).

Sources & evidence

ORD record
ord-f534148277aa4adeb5166c0abb0542ea
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…