Acryloyl chloride → HCID 86721774, compound

HRID 1522170Notes

Reaction equation

HRID 1522170 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]([F:38])([F:37])[O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.[C:39](Cl)(=O)[CH:40]=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:39]=[CH2:40])[CH2:16][CH2:17]2)[C:2]=1[C:31]1[CH:32]=[CH:33][C:28]([O:27][C:26]([F:38])([F:37])[F:25])=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721774HCID 86721774, compound

Procedure

1-(4-(((6-amino-5-(4-(trifluoromethoxy)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-(trifluoromethoxy)phenyl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D, and G. MS: m/z=422 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 8.36 (s, 1H), 7.53 (d, 2H), 7.41 (d, 2H), 7.12 (t, 1H), 6.99 (s, 2H), 6.78 (dd, 1H), 6.07 (dd, 1H), 5.65 (dd, 1H), 4.37 (d, 1H), 4.02 (d, 2H), 3.22 (t, 2H), 2.98 (t, 1H), 2.58 (t, 1H), 1.82 (s, 1H), 1.62 (d, 2H), 0.97 (s, 2H).

Sources & evidence

ORD record
ord-bbdb22aba8724173a6683b89b7308700
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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