N-(3-(Dimethylamino)propyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide → 4-(1-Benzoyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl)-N-(3-dimethylamino-propyl)benzamide

HRID 2074564Notes

Reaction equation

HRID 2074564 reaction equation
I[C:2]1[CH:19]=[N:18][C:5]2[NH:6][CH2:7][CH2:8][N:9]([C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:11])[C:4]=2[CH:3]=1.[CH3:20][N:21]([CH3:43])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:42])[C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][CH:28]=1>>[C:10]([N:9]1[CH2:8][CH2:7][NH:6][C:5]2[N:18]=[CH:19][C:2]([C:30]3[CH:31]=[CH:32][C:27]([C:26]([NH:25][CH2:24][CH2:23][CH2:22][N:21]([CH3:20])[CH3:43])=[O:42])=[CH:28][CH:29]=3)=[CH:3][C:4]1=2)(=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 2758518N-(3-(Dimethylamino)propyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 57886093(7-Iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)phenylmethanone

Product 1

HCID 248530144-(1-Benzoyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl)-N-(3-dimethylamino-propyl)benzamideYield 44%

Procedure

(7-Iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)phenyl-methanone (50 mg) was reacted with N-(3-dimethylamino-propyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide as in General Procedure 4A to give the title compound as a light yellow solid (44% yield). M.p. 94° C., LCMS: m/z=444.20 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.72-1.80 (m, 2H), 2.27 (s, 6H), 2.48-2.53 (t, J=5.8 Hz, 2H), 3.48-3.54 (m, 2H), 3.67-3.73 (m, 2h), 3.98-4.04 (m, 2H), 5.44 (bs, 1H), 7.10-7.18 (m, 2H), 7.36-7.48 (m, 6H), 7.69 (d, J=8.1 Hz, 2H), 8.07 (s, 1H), 8.42 (bs, 1H).

Sources & evidence

ORD record
ord-7b662b56fe4148ceacf782b80f0fc801
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

Loading…