Hydrogen Bromide → HCID 86267820, compound

HRID 709996Notes

Reaction equation

HRID 709996 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([O:13]C)[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28]5[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=5)[CH:23]=4)=[C:17]([CH3:34])[N:16]=3)=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br>C(O)(=O)C>[CH:1]1([NH:6][C:7]2[NH:12][C:11](=[O:13])[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28]5[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=5)[CH:23]=4)=[C:17]([CH3:34])[N:16]=3)=[CH:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 90417742HCID 90417742, compound

Product 1

HCID 86267820HCID 86267820, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Using the procedure of Example 6, N-cyclopentyl-4-methoxy-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-2-amine (0.085 g, 0.186 mmol) and HBr (0.085 mL, 0.743 mmol) were combined in acetic acid (2 mL) to afford 2-(cyclopentylamino)-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (58 mg, 70%). 1H NMR (400 MHz, DMSO-d6): δ 10.78 (br s, 1H), 8.67 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 8.29-8.23 (m, 2H), 7.96 (s, 1H), 7.50 (d, J=8.6 Hz, 1H), 7.22 (d, J=2.4 Hz, 1H), 6.94 (br s, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 4.21-4.18 (m, 1H), 3.84 (s, 3H), 2.34 (s, 3H), 1.92-1.89 (m, 2H), 1.68-1.64 (m, 2H), 1.58-1.54 (m, 2H), 1.49-1.40 (m, 2H); MS (ESI) m/z: 444.2 (M+H+).

Sources & evidence

ORD record
ord-5c4b3b86b3134b168ec5920d4a5f59b2
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

Loading…