Hydrogen Bromide → HCID 86267410, compound

HRID 709990Notes

Reaction equation

HRID 709990 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]([C:25]4[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=4)[CH:20]=3)=[CH:14][N:13]=2)=[CH:6][N:5]=1)[CH3:2].Br>C(O)(=O)C>[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]([C:25]4[CH:26]=[N:27][N:28]([CH3:30])[CH:29]=4)[CH:20]=3)=[CH:14][N:13]=2)=[CH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 90417904HCID 90417904, compound

Product 1

HCID 86267410HCID 86267410, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Using the procedure of Example 7, N-ethyl-4-methoxy-5-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.080 g, 0.20 mmol) was combined with acetic acid (3 mL) and HBr (0.090 mL, 0.79 mmol) to afford 2-(ethylamino)-5-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (40 mg, 51%). 1H NMR (400 MHz, DMSO-d6): δ 11.12 (s, 1H), 8.66 (s, 1H), 8.43 (m, 2H), 8.38 (d, J=5.7 Hz, 1H), 8.26 (s, 1H), 7.97 (d, J=0.7 Hz, 1H), 7.62 (dd, J=8.8, 2.9 Hz, 1H), 7.28 (d, J=2.4 Hz, 1H), 63.80 (br s, 1H), 6.72 (dd, J=5.7, 2.4 Hz, 1H), 3.85 (s, 3H), 3.35 (m, 2H), 1.12 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 390.2 (M+H+).

Sources & evidence

ORD record
ord-59463371c4e443e9b8e9596d156f5fed
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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