3-Aminophenol → HCID 71092807, compound

HRID 1522217Notes

Reaction equation

HRID 1522217 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1I.[NH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.[CH3:36][N:37]([CH3:44])[CH2:38]/[CH:39]=[CH:40]/[C:41](O)=[O:42]>>[NH2:8][C:4]1[C:3]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:27][CH:28]=2)=[C:2]([O:17][C:13]2[CH:12]=[C:11]([NH:10][C:41](=[O:42])/[CH:40]=[CH:39]/[CH2:38][N:37]([CH3:44])[CH3:36])[CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 27343144-Benzyloxy-phenylboronic acidHCID 229365964-Chloro-3-iodopyridin-2-amineHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride

Product 1

HCID 71092807HCID 71092807, compound

Procedure

(E)-N-(3-((2-amino-3-(4-(benzyloxy)phenyl)pyridin-4-yl)oxy)phenyl)-4-(dimethylamino)but-2-enamide was prepared from 4-chloro-3-iodopyridin-2-amine, 3-aminophenol, (4-(benzyloxy)phenyl)boronic acid, and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride using methods A, C, and E. HPLC: 100%. MS: m/z=495 [M+H]+. 1H-NMR (DMSO-D6) δ 10.51 (s, 1H), 9.90 (broad s, 1H), 7.92 (d, 1H), 7.59 (s, 1H), 7.47-7.27 (m, 11H), 7.16 (d, 2H), 6.88 (s, 1H), 6.72 (m, 1H), 6.42 (d, 1H), 6.30 (d, 1H), 5.13 (s, 2H), 3.93 (d, 2H), 2.79 (s, 6H).

Sources & evidence

ORD record
ord-f7853f75e0d64e2ea3e8847fc1a9bd28
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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