Acryloyl chloride → HCID 71473853, compound

HRID 1522264Notes

Reaction equation

HRID 1522264 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[F:10][C@@H:11]1[CH2:16][N:15]([CH2:17][C:18]2[CH:23]=CC(OC)=CC=2)[CH2:14][C@@H:13]([NH2:26])[CH2:12]1.[O:27]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(Cl)(=[O:46])C=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:26][C@H:13]2[CH2:12][C@H:11]([F:10])[CH2:16][N:15]([C:17](=[O:46])[CH:18]=[CH2:23])[CH2:14]2)[C:2]=1[C:37]1[CH:38]=[CH:39][C:34]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 71092853HCID 71092853, compound

Product 1

HCID 71473853HCID 71473853, compound

Procedure

1-((3S,5S)-3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-5-fluoropiperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, (3S,5S)-5-fluoro-1-(4-methoxybenzyl)piperidin-3-amine, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, hydrogenation, and F. HPLC: 97%. MS: m/z=434 [M+H]+.

Sources & evidence

ORD record
ord-69baee623978402f87a8f46fcc983fca
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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