Acryloyl chloride → 4-(4-(4-((((3S,4S)-1-acryloyl-3-hydroxypiperidin-4-yl)methyl)amino)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile

HRID 1522259Notes

Reaction equation

HRID 1522259 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=O)[CH2:14][C@H:13]1[OH:25].CC1(C)C(C)(C)OB([C:34]2[CH:48]=[CH:47][C:37]([O:38][C:39]3[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[CH:41][CH:40]=3)=[CH:36][CH:35]=2)O1.[C:50](Cl)(=O)[CH:51]=C>>[C:18]([N:15]1[CH2:16][CH2:17][C@@H:12]([CH2:11][NH:10][C:7]2[C:2]([C:34]3[CH:48]=[CH:47][C:37]([O:38][C:39]4[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[CH:41][CH:40]=4)=[CH:36][CH:35]=3)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=2)[C@H:13]([OH:25])[CH2:14]1)(=[O:20])[CH:50]=[CH2:51]

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidineHCID 223468894-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]benzonitrileHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 892668444-(4-(4-((((3S,4S)-1-acryloyl-3-hydroxypiperidin-4-yl)methyl)amino)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile

Procedure

4-(4-(4-((((3S,4S)-1-acryloyl-3-hydroxypiperidin-4-yl)methyl)amino)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile (racemic) was prepared from 5,6-dichloropyrimidin-4-amine, (3S,4S)-tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate (racemic), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile, and acryloyl chloride using methods B, C, D, and F. HPLC: 100%. MS: m/z=471 [M+H]+.

Sources & evidence

ORD record
ord-04ab4225153a40c4b9acc7b2c4a62828
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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