(2E)-4-(Dimethylamino)-2-butenoic acid → (E)-4-(dimethylamino)-N-(3-(4-(4-phenoxyphenoxy)pyridin-3-yl)phenyl)but-2-enamide

HRID 1522296Notes

Reaction equation

HRID 1522296 reaction equation
[O:1]([C:8]1[CH:27]=[CH:26][C:11]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:19]2[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=2)[NH2:22])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][N:29]([CH3:36])[CH2:30]/[CH:31]=[CH:32]/[C:33](O)=[O:34]>>[CH3:28][N:29]([CH3:36])[CH2:30]/[CH:31]=[CH:32]/[C:33]([NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[C:19]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:13]=2[O:12][C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:27][CH:26]=2)[CH:20]=1)=[O:34]

Participants

3

Reactant 2

HCID 14805664(2E)-4-(Dimethylamino)-2-butenoic acidHCID 714740103-(4-(4-Phenoxyphenoxy)pyridin-3-yl)aniline

Product 1

HCID 71092913(E)-4-(dimethylamino)-N-(3-(4-(4-phenoxyphenoxy)pyridin-3-yl)phenyl)but-2-enamideYield 35%

Procedure

(E)-4-(dimethylamino)-N-(3-(4-(4-phenoxyphenoxy)pyridin-3-yl)phenyl)but-2-enamide was prepared from 3-(4-(4-phenoxyphenoxy)pyridin-3-yl)aniline and (E)-4-(dimethylamino)but-2-enoic acid using Method E (35% yield). HPLC: 99%, RT=3.399 min. MS: m/z=466 [M+H]+, RT=3.37 min. 1H-NMR (DMSO-d6) δ 10.52 (s, 1H), 8.70 (s, 1H), 8.56 (d, 1H), 8.04 (s, 1H), 7.74 (d, 1H), 7.48 (t, 1H), 7.43-7.38 (m, 3H), 7.29-7.26 (d, 2H), 7.17-7.12 (m, 3H), 7.05-6.99 (m, 3H), 6.74 (m, 1H), 6.48 (d, 1H), 3.94 (d, 2H), 2.79 (s, 6H).

Sources & evidence

ORD record
ord-b737d8cc333545feb343f085a58d8b75
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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