Acryloyl chloride → HCID 86721786, compound

HRID 1522185Notes

Reaction equation

HRID 1522185 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:44])([F:43])[C:27]1[CH:28]=[C:29]([CH:40]=[CH:41][CH:42]=1)[O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=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:34]1[CH:35]=[CH:36][C:31]([O:30][C:29]2[CH:40]=[CH:41][CH:42]=[C:27]([C:26]([F:44])([F:43])[F:25])[CH:28]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 57978431B-[4-[3-(Trifluoromethyl)phenoxy]phenyl]boronic acid

Product 1

HCID 86721786HCID 86721786, compound

Procedure

1-(4-(((6-amino-5-(4-(3-(trifluoromethyl)phenoxy)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-(3-(trifluoromethyl)phenoxy)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 8.36 (s, 1H), 7.68 (t, 1H), 7.55 (d, 1H), 7.50-7.39 (m, 2H), 7.29 (dd, 4H), 7.08 (bs, 1H), 6.93 (bs, 2H), 6.78 (dd, 1H), 6.07 (dd, 1H), 5.64 (dd, 1H), 4.37 (d, 1H), 4.01 (d, 1H), 3.24 (t, 2H), 3.06-2.91 (m, 1H), 2.60 (t, 1H), 1.83 (bs, 1H), 1.62 (d, 2H), 0.98 (m, 2H).

Sources & evidence

ORD record
ord-431f955c8a0b4475abb01762ea99b08d
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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