Acryloyl chloride → HCID 71474496, compound

HRID 1522206Notes

Reaction equation

HRID 1522206 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.C(O[C:15]([N:17]1[CH2:22][CH2:21][C:20]([CH2:25][NH2:26])([O:23][CH3:24])[CH2:19][CH2:18]1)=[O:16])(C)(C)C.[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:43](Cl)(=O)[CH:44]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:26][CH2:25][C:20]2([O:23][CH3:24])[CH2:19][CH2:18][N:17]([C:15](=[O:16])[CH:43]=[CH2:44])[CH2:22][CH2:21]2)[C:2]=1[C:31]1[CH:32]=[CH:33][C:28]([O:27][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 53399259tert-Butyl 4-(aminomethyl)-4-methoxypiperidine-1-carboxylate

Product 1

HCID 71474496HCID 71474496, compound

Procedure

1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-4-methoxypiperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, 4-aminomethyl-4-methoxy-piperidine-1-carboxylic acid tert-butyl ester, (4-phenoxyphenyl)boronic acid and acryloyl chloride according to general scheme 3 using with method S1, S2, S3, and S4C. HPLC purity: 99%. MS: m/z=460 [M+H]+. 1H NMR (CD3OD) δ 8.28 (s, 1H), 7.13-7.43 (m, 9H), 6.77 (m, 1H), 6.17 (d, 1H), 5.75 (d, 1H), 4.27 (d, 1H), 3.85 (d, 1H), 3.62 (s, 2H), 3.83 (m, 1H), 3.22 (s, 3H), 3.04 (m, 1H), 1.79 (m, 2H), 1.44 (m, 2H).

Sources & evidence

ORD record
ord-9de23dd6e90d43a48a1beb78bf427038
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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