HCID 178429763, compound → HCID 86729654, compound

HRID 717554Notes

Reaction equation

HRID 717554 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[NH:18])[C:10]2[C:15]([CH3:16])=[C:14]([F:17])[CH:13]=[N:12][CH:11]=2)[CH:3]=1>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:18]=[C:9]([C:10]3[CH:11]=[N:12][CH:13]=[C:14]([F:17])[C:15]=3[CH3:16])[N:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 1

HCID 178429763HCID 178429763, compound

Product 1

HCID 86729654HCID 86729654, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Lead tetra acetate (0.15 g, 0.00034 mol) was added at RT to a solution of N-(4-chloropyridin-2-yl)-5-fluoro-4-methylnicotinimidamide (40-1; 0.09 g, 0.00034 mol) in toluene (10 mL) in a 40 mL microwave vial. The reaction mixture was heated to 150° C. for 1.5 h under microwave irradiation. It was then cooled to RT, diluted with water (20 mL), and extracted with ethyl acetate (2×30 mL). the combined organic layers were dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was purified by Prep TLC to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.10-9.086 (d, J=8 Hz, 1H), 9.01 (s, 1H), 8.6 (s, 1H), 8.17 (s, 1H), 7.37-7.35 (d, J=8 Hz, 1H), 2.64 (s, 3H), MS (M+1): 263.7.

Workup

  1. temperatureIt was then cooled to RT
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customto afford the crude product, which
  6. customwas purified by Prep TLC

Sources & evidence

ORD record
ord-b78fbcbab279475382cf4a604ebeaebc
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

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