Acryloyl chloride → HCID 71473805, compound

HRID 1522246Notes

Reaction equation

HRID 1522246 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH:11]1[CH2:14][N:13]([C:15]([O:17]C(C)(C)C)=O)[CH2:12]1.[O:22]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:38](Cl)(=O)[CH:39]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH:11]2[CH2:12][N:13]([C:15](=[O:17])[CH:38]=[CH2:39])[CH2:14]2)[C:2]=1[C:26]1[CH:27]=[CH:28][C:23]([O:22][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71473805HCID 71473805, compound

Procedure

1-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)azetidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 3-aminoazetidine-1-carboxylate, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, D, and F. HPLC: 100%. MS: m/z=388 [M+H]+. 1H-NMR (DMSO-d6) δ 8.33 (s, 1H), 7.45 (t, 2H), 7.30-7.13 (m, 8H), 6.83 (broad s, 1.5H), 6.28 (dd, 1H), 6.08 (d, 1H), 5.66 (d, 1H), 4.90 (m, 1H), 4.44 (t, 1H), 1.12 (q, 2H), 3.87 (m, 1H).

Sources & evidence

ORD record
ord-b08f8faf45a04ce58b44aeb6ec894cfb
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

Loading…