Acryloyl chloride → HCID 86721782, compound

HRID 1522180Notes

Reaction equation

HRID 1522180 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]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[C:34]([C:41]([F:44])([F:43])[F:42])[CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:45](Cl)(=O)[CH:46]=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:45]=[CH2:46])[CH2:16][CH2:17]2)[C:2]=1[C:35]1[CH:36]=[CH:37][C:32]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:33][C:34]=1[C:41]([F:44])([F:43])[F:42]

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 71092794HCID 71092794, compound

Product 1

HCID 86721782HCID 86721782, compound

Procedure

1-(4-(((6-amino-5-(4-phenoxy-2-(trifluoromethyl)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-phenoxy-2-(trifluoromethyl)phenyl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D and G. MS: m/z=498 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 8.35 (s, 1H), 7.50 (dd, 2H), 7.39 (m, 2H), 7.28 (t, 1H), 7.19 (d, J=7.8 Hz, 2H), 7.16-7.07 (m, 1H), 7.00 (bs, 1H), 6.78 (dd, 1H), 6.06 (dd, 1H), 5.64 (dd, 1H), 4.36 (d, 1H), 4.01 (d, 1H), 3.16 (m, 2H), 2.97 (t, 1H), 2.65-2.54 (t, 1H), 1.78 (bs, 1H), 1.58 (bs, 2H), 0.97 (bs, 2H).

Sources & evidence

ORD record
ord-95f54cf4ddcb4e8c95748633cff58c1f
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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