3-Aminophenol → HCID 86721851, compound

HRID 1522273Notes

Reaction equation

HRID 1522273 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.CC1(C)C(C)(C)OB([C:26]2[CH:40]=[CH:39][C:29]([O:30][C:31]3[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=3)[C:34]#[N:35])=[CH:28][CH:27]=2)O1.[C:42](Cl)(=[O:45])[CH:43]=[CH2:44]>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:17][C:13]2[CH:12]=[C:11]([NH:10][C:42](=[O:45])[CH:43]=[CH2:44])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:26]1[CH:40]=[CH:39][C:29]([O:30][C:31]2[CH:38]=[CH:37][CH:36]=[C:33]([C:34]#[N:35])[CH:32]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 22346851HCID 22346851, compoundHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721851HCID 86721851, compound

Procedure

N-(3-((6-amino-5-(4-(3-cyanophenoxy)phenyl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile, and acryloyl chloride using methods A, C, and F. HPLC: 98%. MS: m/z=450 [M+H]+. 1H-NMR (DMSO-d6) δ 10.21 (s, 1H), 8.07 (s, 0.5H), 7.61-7.57 (m, 3.5H), 7.49-7.43 (m, 4H), 7.38 (d, 1H), 7.30 (t, 1H), 7.19 (d, 2H), 6.79 (d, 1H), 6.57 (broad s, 1.5H), 6.41 (dd, 1H), 6.25 (d, 1H), 5.76 (d, 1H).

Sources & evidence

ORD record
ord-793382554ac54828b103808f34d6d1a0
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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