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

HRID 1522284Notes

Reaction equation

HRID 1522284 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][C:28]1([F:41])[CH2:33][CH2:32][N:31]([C:34]([O:36]C(C)(C)C)=O)[CH2:30][CH2:29]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:26][CH2:27][C:28]2([F:41])[CH2:29][CH2:30][N:31]([C:34](=[O:36])/[CH:47]=[CH:46]/[CH2:45][N:44]([CH3:51])[CH3:43])[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 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 40152119tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylateHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride

Product 1

HCID 71093096(E)-1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-4-fluoropiperidin-1-yl)-4-(dimethylamino)but-2-en-1-oneYield 15.9%

Procedure

(E)-1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-4-fluoropiperidin-1-yl)-4-(dimethylamino)but-2-en-1-one was prepared 5,6-dichloropyrimidin-4-amine, 4-phenoxyphenylboronic acid, tert-butyl 4-(aminomethyl)-4-fluoropiperidine-1-carboxylate and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride with method S1, S2, S3, S4A. Yield 15.9%. 1H NMR (CD3OD) δ 8.26 (s, 1H), 7.14-7.40 (m, 9H), 6.93 (d, 1H), 6.74 (m, 1H), 4.47 (d, 1H), 3.98 (m, 3H), 3.75 (d, 2H), 3.41 (t, 1H), 3.03 (t, 1H), 2.97 (m, 6H), 1.81 (m, 2H), 1.62 (m, 2H). HPLC PURITY: 99%, MS: m/z=505[M+H]+

Sources & evidence

ORD record
ord-573ac6401ac54e2398da7d13835bfba8
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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