Acryloyl chloride → HCID 86721849, compound

HRID 1522270Notes

Reaction equation

Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C@H:11]1[C@H:16]([OH:17])[CH2:15][CH2:14][N:13]([C:18]([O:20]CC2C=CC=CC=2)=O)[CH2:12]1.[O:28]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:44](Cl)(=O)[CH:45]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][C@H:11]2[C@H:16]([OH:17])[CH2:15][CH2:14][N:13]([C:18](=[O:20])[CH:44]=[CH2:45])[CH2:12]2)[C:2]=1[C:32]1[CH:33]=[CH:34][C:29]([O:28][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:30][CH:31]=1

Participants

Reactant 4

HCID 13140Acryloyl chloride

HCID 27343774-Phenoxyphenylboronic acid

HCID 10682118HCID 10682118, compound

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

Product 1

HCID 86721849HCID 86721849, compound

Procedure

1-((3R,4R)-3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-4-hydroxypiperidin-1-yl)prop-2-en-1-one (racemic) was prepared from 5,6-dichloropyrimidin-4-amine, (3R,4R)-benzyl 3-amino-4-hydroxypiperidine-1-carboxylate (racemic), (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, hydrogenation, and F. HPLC: 100%. MS: m/z=432 [M+H]+.

Sources & evidence

ORD record: ord-d3156790064a4c4e97986b8e10645c8a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073947B2

Reaction notes

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