Acryloyl chloride → HCID 86721761, compound

HRID 1522148Notes

Reaction equation

HRID 1522148 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[CH3:10][NH:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21]C(C)(C)C)=O)[CH2:15][CH2:14]1.[O:26]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:42](Cl)(=O)[CH:43]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([N:11]([CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19](=[O:21])[CH:42]=[CH2:43])[CH2:17][CH2:18]2)[CH3:10])[C:2]=1[C:30]1[CH:31]=[CH:32][C:27]([O:26][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 21934652tert-Butyl 4-((methylamino)methyl)piperidine-1-carboxylateHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721761HCID 86721761, compound

Procedure

1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)(methyl)amino)methyl)piperidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-((methylamino)methyl)piperidine-1-carboxylate, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, D, and F. HPLC purity: 100%. MS: m/z=444 [M+H]+. 1H-NMR (DMSO-d6) δ 8.32 (s, 1H), 7.45 (t, 2H), 7.33 (d, 2H), 7.20 (t, 1H), 7.12 (t, 4H), 6.95 (broad s, 1.5H), 6.77 (dd, 1H), 6.07 (d, 1H), 5.65 (d, 1H), 4.38 (d, 1H), 4.01 (d, 1H), 3.36 (m, 2H), 2.99 (t, 1H), 2.68 (s, 3H), 2.57 (t, 1H), 1.92 (s, 1H), 1.50 (d, 2H), 0.97 (t, 2H).

Sources & evidence

ORD record
ord-8f1a61bbc60143589b40c2a80f648bc0
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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