4-Phenoxyphenylboronic acid → (E)-1-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one

HRID 1522211Notes

Reaction equation

HRID 1522211 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].[O:26]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl.[CH3:43][N:44]([CH3:51])[CH2:45]/[CH:46]=[CH:47]/C(O)=O>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][C@@H:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])/[CH:47]=[CH:46]/[CH2:45][N:44]([CH3:51])[CH3:43])[CH2:14][C@H:13]2[OH:25])[C:2]=1[C:30]1[CH:31]=[CH:32][C:27]([O:26][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 27343774-Phenoxyphenylboronic acidHCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride

Product 1

HCID 71092950(E)-1-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one

Procedure

(E)-1-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, (3S,4S)-tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate, (4-phenoxyphenyl)boronic acid and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride according to general scheme 3 using methods S1, S2, S3, and S4D. HPLC purity: 99%. MS: m/z=503 [M+H]+. 1H NMR (CD3OD) δ 8.26 (s, 1H), 7.10-7.45 (m, 9H), 6.91 (d, 1H), 6.67 (m, 1H), 4.54 (m, 1H), 4.02 (m, 1H), 3.97 (m, 2H), 3.74 (m, 1H), 3.51 (m, 1H), 3.00 (m, 1H), 2.62 (m, 1H), 1.76 (m, 2H), 1.23 (m, 1H).

Sources & evidence

ORD record
ord-4b3a7597e441438ab250e71ac2d2a0a4
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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