Acryloyl chloride → HCID 86721773, compound

HRID 1522169Notes

Reaction equation

HRID 1522169 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.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.[C:35](Cl)(=O)[CH:36]=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:35]=[CH2:36])[CH2:16][CH2:17]2)[C:2]=1[C:29]1[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 2856454-Fluorophenylboronic acidHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721773HCID 86721773, compound

Procedure

1-(4-(((6-amino-5-(4-fluorophenyl)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-fluorophenyl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D and G. MS: m/z=356 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 8.35 (s, 1H), 7.40 (t, 2H), 7.32 (dd, 2H), 7.07 (t, 1H), 6.95 (s, 2H), 6.78 (dd, 1H), 6.07 (dd, 1H), 5.65 (dd, 1H), 4.37 (d, 2H), 4.01 (d, 2H), 3.21 (t, 2H), 2.98 (t, 1H), 2.67-2.53 (m, 1H), 1.82 (s, 1H), 1.61 (d, 2H), 0.98 (d, 2H).

Sources & evidence

ORD record
ord-988c54cd6790459e9726382ded77668c
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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