3-Aminophenol → HCID 86721769, compound

HRID 1522161Notes

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:27]=[N:28][N:29]([CH2:31][C:32]3[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=3)[CH:30]=2)O1.[C:41](Cl)(=[O:44])[CH:42]=[CH2:43]>>[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:41](=[O:44])[CH:42]=[CH2:43])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:26]1[CH:27]=[N:28][N:29]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]#[N:37])=[CH:38][CH:39]=2)[CH:30]=1

Participants

Reactant 4

HCID 115683-Aminophenol

HCID 13140Acryloyl chloride

HCID 242192625,6-Dichloro-pyrimidin-4-ylamine

HCID 68571721HCID 68571721, compound

Product 1

HCID 86721769HCID 86721769, compound

Procedure

N-(3-((6-amino-5-(1-(4-cyanobenzyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile, and acryloyl chloride using methods A, C, and F. HPLC purity: 97%. MS: m/z=438 [M+H]+. 1H-NMR (DMSO-d6) δ 10.21 (s, 1H), 8.18 (s, 1H), 8.03 (s, 1H), 7.82 (d, 2H), 7.76 (s, 1H), 7.52 (s, 1H), 7.42 (d, 2H), 7.40 (d, 1H), 7.30 (t, 1H), 6.89-6.67 (m, 2.5H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.77 (d, 1H), 5.49 (s, 2H).

Sources & evidence

ORD record: ord-164e841516274db2a1bc7a29c0017ab9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073947B2

Reaction notes

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