Acryloyl chloride → HCID 71474586, compound

HRID 1522233Notes

Reaction equation

HRID 1522233 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][C:12]1([OH:25])[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=O)[CH2:14][CH2:13]1.[F:26][C:27]([F:45])([F:44])[C:28]1[CH:29]=[C:30]([CH:41]=[CH:42][CH:43]=1)[O:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.[C:46](Cl)(=O)[CH:47]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][C:12]2([OH:25])[CH2:13][CH2:14][N:15]([C:18](=[O:20])[CH:46]=[CH2:47])[CH2:16][CH2:17]2)[C:2]=1[C:35]1[CH:36]=[CH:37][C:32]([O:31][C:30]2[CH:41]=[CH:42][CH:43]=[C:28]([C:27]([F:45])([F:44])[F:26])[CH:29]=2)=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 23396319tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylateHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 57978431B-[4-[3-(Trifluoromethyl)phenoxy]phenyl]boronic acid

Product 1

HCID 71474586HCID 71474586, compound

Procedure

1-(4-(((6-amino-5-(4-(3-(trifluoromethyl)phenoxy)phenyl)pyrimidin-4-yl)amino)methyl)-4-hydroxypiperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate, (4-(3-(trifluoromethyl)phenoxy)phenyl)boronic acid, and acryloyl chloride using methods B, C, D, and F. HPLC: 99%. MS: m/z=514 [M+H]+. 1H NMR (500 MHz, dmso) δ 7.88 (s, 1H), 7.57 (t, J=7.9 Hz, 1H), 7.44 (d, J=7.8 Hz, 1H), 7.38 (s, 1H), 7.32 (dd, J=8.2, 2.3 Hz, 1H), 7.22 (dd, J=6.5, 4.6 Hz, 2H), 7.14 (t, 2H), 6.71 (dd, 10.5 Hz, 1H), 5.99 (dd, 1H), 5.63-5.52 (m, 3H), 5.15 (t, 1H), 5.09 (s, 1H), 3.94 (d, 1H), 3.66 (d, 1H), 2.96 (t, 1H), 1.40-1.20 (m, 5H), 0.79 (t, 1H).

Sources & evidence

ORD record
ord-c9c8120ae9b2462db859d1c7de9e04aa
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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