Pyridine → N-[5-(3-Fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-yl]propanamide

HRID 1710725Notes

Reaction equation

[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[CH:10][C:11]([NH2:20])=[N:12][C:13]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.N1C=CC=CC=1.[C:27](Cl)(=[O:30])[CH2:28][CH3:29]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[CH:10][C:11]([NH:20][C:27](=[O:30])[CH2:28][CH3:29])=[N:12][C:13]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-amine (Example 115) (150 mg, 0.56 mmol) in CH2Cl2 (5 mL) was added pyridine (1 mL), cooled at 0° C., propionyl chloride (57 mg, 0.62 mmol) was added dropwise. Upon complete addition, the ice bath was removed and the reaction continued at room temperature overnight. Then CH2Cl2 (10 mL) and aqueous NaOH 10% (10 mL) were added, the organic layer was separated, and washed with H2O and saturated NaCl. The combined organic layers were dried over Na2SO4, filtered and concentrated in vaccuo. The crude product was purified by column chromatography on silica gel, eluting with an EtOAc/hexane gradient (80-100%), yielding the target product (100 mg, 55%)

Workup

additionUpon complete addition
customthe ice bath was removed
additionThen CH2Cl2 (10 mL) and aqueous NaOH 10% (10 mL) were added
customthe organic layer was separated
washwashed with H2O and saturated NaCl
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vaccuo
customThe crude product was purified by column chromatography on silica gel
washeluting with an EtOAc/hexane gradient (80-100%)

Sources & evidence

ORD record: ord-672261d3fac243e385ebfda0f4cffcc3
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790728B2

Reaction notes

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