5-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)pyridin-2-amine → HCID 86270404, compound

HRID 2278988Notes

Reaction equation

HRID 2278988 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)[CH:4]=[N:3]1.[CH3:21][C:22]1([CH3:37])[CH2:27][CH:26]([N:28]2[CH2:32][CH2:31][N:30]([C:33](Cl)=[O:34])[C:29]2=[O:36])[CH2:25][CH2:24][O:23]1>C(Cl)Cl>[CH3:21][C:22]1([CH3:37])[CH2:27][CH:26]([N:28]2[CH2:32][CH2:31][N:30]([C:33]([NH:20][C:17]3[CH:16]=[CH:15][C:14]([O:13][C:11]4[CH:10]=[CH:9][N:8]=[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)[CH:12]=4)=[CH:19][N:18]=3)=[O:34])[C:29]2=[O:36])[CH2:25][CH2:24][O:23]1

Participants

4

Reactant 2

HCID 593227775-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)pyridin-2-amineHCID 90426111HCID 90426111, compound

Product 1

HCID 86270404HCID 86270404, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 0° C. solution of Example A2 (0.060 g, 0.224 mmol) and TEA (0.094 mL, 0.673 mmol) in DCM (1 mL) was treated with a solution of crude 3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-2-oxoimidazolidine-1-carbonyl chloride (0.088 g, 0.337 mmol) in DCM (1 mL). The mixture was warmed to RT, stirred for 0.5 h, then concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-N-(5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide as an off-white solid (74 mg, 67%). 1H NMR (400 MHz, DMSO-d6): δ 10.96 (s, 1 H), 8.36 (d, J=5.7 Hz, 1 H), 8.25 (s, 1 H), 8.21 (m, 1 H), 8.05 (m, 1 H), 7.96 (d, J=0.7 Hz, 1 H), 7.72 (dd, J=9.0, 2.9 Hz, 1 H), 7.23 (d, J=2.4 Hz, 1 H), 6.68 (dd, J=5.7, 2.4 Hz, 1 H), 4.04 (m, 1 H), 3.84 (s, 3 H), 3.84-3.75 (m, 2 H), 3.70-3.59 (m, 2 H), 3.46-3.39 (m, 2 H), 1.60-1.47 (m, 4 H), 1.18 (d, J=15.1 Hz, 6 H); MS (ESI) m/z: 492.2 (M+H+).

Workup

  1. concentrationconcentrated to dryness
  2. custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-48d89052cd62451eb8119b2a5c8b84f6
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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