2-Propenoic acid, 3-phenyl- → HCID 86721857, compound

HRID 1522285Notes

Reaction equation

HRID 1522285 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[O:10]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36]C(C)(C)C)=O)[CH2:30][CH2:29]1.C(O)(=O)[CH:42]=[CH:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:26][CH2:27][CH:28]2[CH2:29][CH2:30][N:31]([C:34](=[O:36])/[CH:42]=[CH:43]/[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:32][CH2:33]2)[C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 87842-Propenoic acid, 3-phenyl-HCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721857HCID 86721857, compoundYield 45.4%

Procedure

(E)-1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)-3-phenylprop-2-en-1-one was prepared 5,6-dichloropyrimidin-4-amine, 4-phenoxyphenylboronic acid, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate and cinnamic acid with method S1, S2, S3, S4A. Yield 45.4%. 1H NMR (CD3OD) δ 8.04 (s, 1H), 7.19-7.47 (m, 14H), 4.55 (d, 1H), 4.25 (d, 1H), 3.42 (d, 2H), 3.14 (t, 1H), 2.75 (t, 1H), 2.00 (m, 1H), 1.76 (t, 2H), 1.15 (m, 2H). HPLC PURITY: 98%, MS: m/z=506[M+H]+

Sources & evidence

ORD record
ord-8b3d06cd5518465c917b88b85221ec98
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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