Acryloyl chloride → 1-(4-(((6-Amino-5-(4-(pyridin-4-yloxy)phenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one

HRID 1522187Notes

Reaction equation

HRID 1522187 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.[N:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=2)=[CH:27][CH:26]=1.[C:41](Cl)(=O)[CH:42]=C>>[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](=[O:20])[CH:41]=[CH2:42])[CH2:16][CH2:17]2)[C:2]=1[C:35]1[CH:36]=[CH:37][C:32]([O:31][C:28]2[CH:29]=[CH:30][N:25]=[CH:26][CH:27]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 576553424-(Pyridin-4-yloxy)phenylboronic acid

Product 1

HCID 867217881-(4-(((6-Amino-5-(4-(pyridin-4-yloxy)phenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one

Procedure

1-(4-(((6-amino-5-(4-(pyridin-4-yloxy)phenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, (4-(pyridin-4-yloxy)phenyl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D and G. MS: m/z=431 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 9.20 (s, 1H), 8.90 (d, 1H), 8.39 (s, 1H), 8.18 (m, 2H), 7.55-7.36 (m, 4H), 7.03 (s, 2H), 6.78 (dd, 1H), 6.07 (dd, 1H), 5.65 (dd, 1H), 4.85 (t, 2H), 4.38 (d, 1H), 4.02 (d, 1H), 3.25 (t, 2H), 3.14 (t, 2H), 3.06-2.94 (m, 2H), 2.65-2.54 (m, 1H), 1.84 (bs, 1H), 1.62 (d, 2H), 1.00 (m, 2H).

Sources & evidence

ORD record
ord-74aa0cff90614318935f98d68baa6522
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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