Hydrogen Bromide → HCID 86267407, compound

HRID 709984Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[N:9]=[C:8]([O:10]C)[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]4)[CH:20]=3)=[C:14]([CH3:31])[N:13]=2)=[CH:6][N:5]=1)[CH3:2].Br>>[CH2:1]([NH:3][C:4]1[NH:9][C:8](=[O:10])[C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]4)[CH:20]=3)=[C:14]([CH3:31])[N:13]=2)=[CH:6][N:5]=1)[CH3:2]

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 90417816HCID 90417816, compound

Product 1

HCID 86267407HCID 86267407, compoundYield 51.3%

Procedure

Using the procedure of Example 1, N-ethyl-4-methoxy-5-(6-methyl-5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.12 g, 0.29 mmol) and 48% HBr (0.63 mL, 11.5 mmol) were combined to afford 2-(ethylamino)-5-(6-methyl-5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one as a white solid (0.06 g, 51%). 1H NMR (400 MHz, DMSO-d6): δ 10.60 (br s, 1H), 8.68 (s, 1H), 8.40 (d, J=1.3 Hz, 1H), 8.31-8.30 (m, 2H), 7.64 (s, 1H), 7.54 (d, J=8.6 Hz, 1H), 7.39 (d, J=2.2 Hz, 1H), 6.93 (br s, 1H), 6.73 (dd, J=5.8, 2.2 Hz, 1H), 3.35-3.33 (m, 2H), 2.35 (s, 3H), 2.13 (s, 3H), 1.12 (t, J=7.1 Hz, 3H); MS (ESI) m/z: 404.2 (M+H+).

Sources & evidence

ORD record: ord-632c2a55b1dc48c4931fc2d84d7158da
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181223B2

Reaction notes

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