(2E)-4-(Dimethylamino)-2-butenoic acid → HCID 71092797, compound

HRID 1522298Notes

Reaction equation

HRID 1522298 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[CH3:29][N:30]([CH3:37])[CH2:31]/[CH:32]=[CH:33]/[C:34](O)=[O:35]>>[NH2:13][C:9]1[N:10]=[CH:11][N:12]=[C:7]([O:6][C:5]2[CH:27]=[CH:28][C:2]([NH:1][C:34](=[O:35])/[CH:33]=[CH:32]/[CH2:31][N:30]([CH3:37])[CH3:29])=[CH:3][CH:4]=2)[C:8]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 14805664(2E)-4-(Dimethylamino)-2-butenoic acidHCID 71473957HCID 71473957, compound

Product 1

HCID 71092797HCID 71092797, compoundYield 29%

Procedure

(E)-N-(4-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)phenyl)-4-(dimethylamino)but-2-enamide was prepared from 6-(4-aminophenoxy)-5-(4-phenoxyphenyl)pyrimidin-4-amine and (E)-4-(dimethylamino)but-2-enoic acid using Method E (29% yield). HPLC: 99%, RT=3.448 min. MS: m/z=482 [M+H]+, RT=3.40 min. 1H-NMR (DMSO-d6) δ 10.30 (s, 1H), 8.02 (s, 1H), 7.62 (d, 2H), 7.43-7.38 (m, 4H), 7.15 (tt, 1H), 7.10-7.01 (m, 6H), 6.73 (m, 1H), 6.49 (broad s, 2H), 6.44 (d, 1H), 3.93 (m, 2H), 2.80 (s, 6H).

Sources & evidence

ORD record
ord-c627afb9c8894951be65e1fb00679fa8
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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