Acryloyl chloride → HCID 71474393, compound

HRID 1522175Notes

Reaction equation

HRID 1522175 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]1[CH2:30][CH2:29][O:28][C:27]2[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:26]1=2.[C:38](Cl)(=O)[CH:39]=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:38]=[CH2:39])[CH2:16][CH2:17]2)[C:2]=1[C:32]1[CH:33]=[CH:34][C:26]2[O:25][CH2:30][CH2:29][O:28][C:27]=2[CH:31]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 2776178(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71474393HCID 71474393, compound

Procedure

1-(4-(((6-amino-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)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, (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D and G. MS: m/z=396 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 8.33 (s, 1H), 7.07 (d, 1H), 7.04 (d, 1H), 6.93 (s, 2H), 6.83-6.73 (m, 2H), 6.70 (dd, 1H), 6.07 (dd, 1H), 5.65 (dd, 1H), 4.36 (d, 1H), 4.30 (s, 3H), 4.01 (d, 1H), 3.22 (s, 3H), 2.98 (t, 1H), 2.66-2.53 (m, 1H), 1.83 (m, 1H), 1.61 (d, 2H), 1.10-0.83 (m, 2H).

Sources & evidence

ORD record
ord-a01f991c7c16400b80a591b6a8a532d8
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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