Acryloyl chloride → HCID 86721846, compound

HRID 1522267Notes

Reaction equation

HRID 1522267 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH:11]1[CH2:24][C:13]2([CH2:16][N:15]([C:17]([O:19]C(C)(C)C)=O)[CH2:14]2)[CH2:12]1.CC1(C)C(C)(C)OB([C:33]2[CH:47]=[CH:46][C:36]([O:37][C:38]3[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=3)=[CH:35][CH:34]=2)O1.[C:49](Cl)(=O)[CH:50]=C>>[C:17]([N:15]1[CH2:14][C:13]2([CH2:12][CH:11]([NH:10][C:7]3[C:2]([C:33]4[CH:47]=[CH:46][C:36]([O:37][C:38]5[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=5)=[CH:35][CH:34]=4)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=3)[CH2:24]2)[CH2:16]1)(=[O:19])[CH:49]=[CH2:50]

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 223468894-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]benzonitrileHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 46930560tert-Butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate

Product 1

HCID 86721846HCID 86721846, compound

Procedure

4-(4-(4-((2-acryloyl-2-azaspiro[3.3]heptan-6-yl)amino)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 6-amino-2-azaspiro[3.3]heptane-2-carboxylate, 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile, and acryloyl chloride using methods B, C, D, and E. HPLC: 98%. MS: m/z=453 [M+H]+. 1H-NMR (DMSO-d6) δ 7.96 (s, 1H), 7.87 (d, 2H), 7.29-7.23 (m, 6H), 6.31-6.22 (m, 1H), 6.07 (d, 1H), 5.67-5.46 (m, 4H), 4.40 (q, 1H), 4.25 (s, 1H), 4.08 (s, 1H), 3.96 (s, 1H), 3.79 (s, 1H), 2.47-2.40 (m, 2H), 2.14-2.09 (m, 2H).

Sources & evidence

ORD record
ord-941b73c0e7334dd8affbe422b52a3d46
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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