Acryloyl chloride → HCID 71474444, compound

HRID 1522179Notes

Reaction equation

HRID 1522179 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.[CH3:25][N:26]1[CH2:31][CH2:30][CH:29]([O:32][C:33]2[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=2)[CH2:28][CH2:27]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:36]1[CH:37]=[CH:38][C:33]([O:32][CH:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)=[CH:34][CH:35]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 71093030HCID 71093030, compound

Product 1

HCID 71474444HCID 71474444, compound

Procedure

1-(4-(((6-amino-5-(4-((1-methylpiperidin-4-yl)oxy)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-((1-methylpiperidin-4-yl)oxy)phenyl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D and G. MS: m/z=451 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 9.79 (s, 1H), 8.35 (s, 1H), 7.19 (m, 5H), 6.93 (m, 3H), 6.78 (dd, 1H), 6.07 (dd, 1H), 5.65 (dd, 1H), 4.81 (s, 1H), 4.60 (s, 1H), 4.37 (d, 1H), 4.01 (d, 1H), 3.19 (d, 5H), 2.98 (t, 1H), 2.85 (d, 4H), 2.65-2.53 (m, 1H), 2.29 (d, 1H), 2.06 (d, 2H), 1.81 (d, 2H), 1.59 (s, 2H), 1.33-1.16 (m, 1H), 1.06-0.82 (m, 2H).

Sources & evidence

ORD record
ord-96800a0fda064b0fa715183a6e68a239
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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