2,6-Diaminopyridine → HCID 86721817, compound

HRID 1522231Notes

Reaction equation

HRID 1522231 reaction equation
Br[C:2]1[C:3](Cl)=[N:4][CH:5]=[N:6][CH:7]=1.[N:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:16].[O:17]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:33](Cl)(=[O:36])[CH:34]=[CH2:35]>>[O:17]([C:24]1[CH:29]=[CH:28][C:27]([C:2]2[C:3]([NH:15][C:14]3[N:9]=[C:10]([NH:16][C:33](=[O:36])[CH:34]=[CH2:35])[CH:11]=[CH:12][CH:13]=3)=[N:4][CH:5]=[N:6][CH:7]=2)=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 88612,6-DiaminopyridineHCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 122700785-Bromo-4-chloropyrimidine

Product 1

HCID 86721817HCID 86721817, compound

Procedure

N-(6-((5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)pyridin-2-yl)acrylamide was prepared from 5-bromo-4-chloropyrimidine, pyridine-2,6-diamine, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods H, C, and F. HPLC: 97%. MS: m/z=410 [M+H]+. 1H-NMR (DMSO-D6) δ 10.43 (s, 1H), 8.75 (s, 1H), 8.33 (s, 1H), 8.04 (broad s, 1H), 7.85-7.73 (m, 3H), 7.48 (d, 2H), 7.39 (t, 2H), 7.15 (t, 1H), 7.07 (d, 2H), 7.03 (d, 2H), 6.47 (dd, 1H), 6.22 (d, 1H), 5.70 (d, 1H).

Sources & evidence

ORD record
ord-adc5208ac79549a8a8571ccc556bbc98
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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