Acryloyl chloride → HCID 86721852, compound

HRID 1522274Notes

Reaction equation

HRID 1522274 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.CC1(C)C(C)(C)OB([C:33]2[CH:47]=[CH:46][C:36]([O:37][C:38]3[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=3)[C:41]#[N:42])=[CH:35][CH:34]=2)O1.[C:49](Cl)(=O)[CH:50]=C>>[C:18]([N:15]1[CH2:14][CH2:13][CH:12]([CH2:11][NH:10][C:7]2[C:2]([C:33]3[CH:47]=[CH:46][C:36]([O:37][C:38]4[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=4)[C:41]#[N:42])=[CH:35][CH:34]=3)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=2)[CH2:17][CH2:16]1)(=[O:20])[CH:49]=[CH2:50]

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 22346851HCID 22346851, compoundHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721852HCID 86721852, compound

Procedure

3-(4-(4-(((1-acryloylpiperidin-4-yl)methyl)amino)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile, and acryloyl chloride using methods B, C, D, and F. HPLC: 100%. MS: m/z=455 [M+H]+. 1H-NMR (DMSO-d6) δ 7.96 (s, 1H), 7.63-7.56 (m, 3H), 7.50-7.45 (m, 1H), 7.29-7.19 (m, 4H), 6.78 (dd, 1H), 6.06 (d, 1H), 5.63 (d, 1H), 5.58-5.42 (m, 3H), 4.36 (d, 1H), 4.00 (d, 1H), 3.15 (t, 2H), 2.96 (t, 1H), 2.58 (t, 1H), 1.90-1.78 (m, 1H), 1.69-1.55 (m, 2H), 1.04-0.87 (m, 2H).

Sources & evidence

ORD record
ord-3b89954c97c14d8f9039f685df5de815
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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