Potassium Carbonate → HCID 11428061, compound

HRID 2109936Notes

Reaction equation

Br[C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:17]([C:21]1[CH:25]=[C:24]([NH2:26])[N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[N:22]=1)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:17]([C:21]1[CH:25]=[C:24]([NH:26][C:2]2[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=2)[N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[N:22]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 3-bromopyridine-2-carboxylic acid (71 mg, 0.35 mmol), potassium carbonate (53 mg, 0.39 mmol), 3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (80 mg, 0.35 mmol) (Intermediate F), and copper (II) acetate (1.3 mg, 0.007 mmol) in DMF (1 mL) was heated (150° C.) in a sealed tube for 16 h. The mixture was cooled to rt, filtered through with a silica gel plug using ethyl acetate as eluent. The mixture was concentrated to dryness and subjected to HPLC purification using a gradient elution from 30% to 90% acetonitrile in water to afford 2.8 mg (2.3%) of the desired product. 1H NMR (300 MHz, CD3OD) δ 8.11 (dd, 2H), 7.79 (dd, 1H), 7.32-7.45 (m, 4H), 6.45 (s, 1H), 2.11 (s, 3H), 1.40 (s, 9H); ES-MS m/z 351.0 (MH+), HPLC RT (min) 2.46.

Workup

temperatureThe mixture was cooled to rt
filtrationfiltered through with a silica gel plug
concentrationThe mixture was concentrated to dryness
customsubjected to HPLC purification
washa gradient elution from 30% to 90% acetonitrile in water

Sources & evidence

ORD record: ord-704a83680b3048ac8c1a439aed1bbedd
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517878B2

Reaction notes

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