Acryloyl chloride → HCID 86721805, compound

HRID 1522207Notes

Reaction equation

HRID 1522207 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH:11]1[CH2:25][C:13]2([CH2:16][CH:15]([NH:17][C:18](=[O:24])OC(C)(C)C)[CH2:14]2)[CH2:12]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]([NH:10][CH:11]2[CH2:12][C:13]3([CH2:14][CH:15]([NH:17][C:18](=[O:24])[CH:42]=[CH2:43])[CH2:16]3)[CH2:25]2)[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 16228708tert-Butyl (6-aminospiro[3.3]heptan-2-yl)carbamateHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721805HCID 86721805, compound

Procedure

N-(6-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)spiro[3.3]heptan-2-yl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl (6-aminospiro[3.3]heptan-2-yl)carbamate, (4-phenoxyphenyl)boronic acid and acryloyl chloride according to general scheme 3 using methods S1, S2, S3, and S4C. HPLC purity: 95%. MS: m/z=442 [M+H]+. 1H NMR (CD3OD) δ 8.23 (s, 1H), 7.10-7.46 (m, 9H), 6.23 (m, 1H), 5.66 (m, 1H), 4.59 (m, 1H), 3.69 (m, 1H), 3.19 (d, 1H), 2.54 (m, 2H), 2.08-2.34 (m, 6H).

Sources & evidence

ORD record
ord-17407b3ac98a4e4ba2ea5d37d7b1820c
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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