Acryloyl chloride → HCID 86721785, compound

HRID 1522184Notes

Reaction equation

HRID 1522184 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.[OH:25][C:26]1[CH:41]=[CH:40][C:29]([O:30][C:31]2[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=2)=[CH:28][CH:27]=1.[C:42](Cl)(=O)[CH:43]=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:42]=[CH2:43])[CH2:16][CH2:17]2)[C:2]=1[C:34]1[CH:35]=[CH:36][C:31]([O:30][C:29]2[CH:40]=[CH:41][C:26]([OH:25])=[CH:27][CH:28]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 71092964HCID 71092964, compound

Product 1

HCID 86721785HCID 86721785, compound

Procedure

1-(4-(((6-amino-5-(4-(4-hydroxyphenoxy)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-(4-hydroxyphenoxy)phenyl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D and G. MS: m/z=446 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 9.39 (bs, 1H), 8.31 (s, 1H), 7.54 (t, 1H), 7.06 (dd, 2H), 7.00 (d, 2H), 6.94 (d, 1H), 6.89 (bs, 1H), 6.79 (d, 2H), 6.72 (bs, 1H), 6.08 (dd, 1H), 5.66 (dd, 1H), 4.38 (d, 1H), 4.01 (d, J1H), 3.21 (d, 2H), 2.97 (t, 1H), 2.63-2.54 (m, 1H), 1.81 (bs, 1H), 1.58 (d, 2H), 0.96 (bs, 2H).

Sources & evidence

ORD record
ord-75a7b659078e4648993c6f9b23815a04
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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