Acryloyl chloride → HCID 86721790, compound

HRID 1522189Notes

Reaction equation

HRID 1522189 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.[CH:25]1([O:31][C:32]2[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]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:34]=[CH:33][C:32]([O:31][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[CH:37][CH:36]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 222898184-Cyclohexyloxy-benzeneboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721790HCID 86721790, compound

Procedure

1-(4-(((6-amino-5-(4-(cyclohexyloxy)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-(cyclohexyloxy)phenyl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D and G. MS: m/z=436 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 8.34 (s, 1H), 7.13 (dd, 4H), 7.00 (t, 1H), 6.95-6.83 (bs, 2H), 6.78 (dd, 1H), 6.07 (d, 1H), 5.64 (d, 1H), 4.38 (bs, 2H), 4.01 (d, 1H), 3.22 (t, 2H), 2.98 (t, 1H), 2.58 (t, 1H), 1.97 (bs, 2H), 1.91-1.67 (m, 3H), 1.67-1.21 (m, 8H), 1.07-0.86 (m, 2H).

Sources & evidence

ORD record
ord-a54b822bdba1420995c8759a37593c4a
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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