1-Boc-4-(aminomethyl)piperidine → 4-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)piperidine-1-carbonyl)-1-methylpyridin-2(1H)-one

HRID 1522113Notes

Reaction equation

HRID 1522113 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=O)[CH2:14][CH2:13]1.[O:25]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:41][N:42]1[CH:47]=[CH:46][C:45](C(O)=O)=[CH:44][C:43]1=[O:51]>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([C:18]([C:45]3[CH:46]=[CH:47][N:42]([CH3:41])[C:43](=[O:51])[CH:44]=3)=[O:20])[CH2:16][CH2:17]2)[C:2]=1[C:29]1[CH:30]=[CH:31][C:26]([O:25][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 7368171-Boc-4-(aminomethyl)piperidineHCID 8199231-Methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 711132904-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)piperidine-1-carbonyl)-1-methylpyridin-2(1H)-one

Procedure

4-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)piperidine-1-carbonyl)-1-methylpyridin-2(1H)-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, (4-phenoxyphenyl)boronic acid, and 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid using methods B, C, D, and E. HPLC purity: 100%. MS: m/z=511 [M+H]+. 1H-NMR (DMSO-d6) δ 8.28 (s, 1H), 7.69 (d, 1H), 7.38 (t, 2H), 7.20 (d, 2H), 7.14-6.90 (m, 8H), 6.19 (s, 1H), 6.06 (d, 1H), 1.28 (d, 1H), 3.47 (d, 1H), 3.35 (s, 3H), 3.18 (s, 2H), 2.90 (t, 1H), 2.61 (t, 1H), 1.76 (s, 1H), 1.58 (d, 1H), 1.48 (d, 1H), 1.04-0.92 (m, 2H).

Sources & evidence

ORD record
ord-ddbfaceecc39487e830d01b8c68c1103
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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