HCID 178441585, compound → HCID 178441558, compound

HRID 75191Notes

Reaction equation

HRID 75191 reaction equation
[C:1]([C:5]1[NH:6][C:7]([C:18]2[C:19](F)=[N:20][CH:21]=[CH:22][CH:23]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[NH2:17])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:1]([C:5]1[NH:6][C:7]2[C:18]3[CH:23]=[CH:22][CH:21]=[N:20][C:19]=3[NH:17][C:11]3[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=3[C:8]=2[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 178441585HCID 178441585, compound

Product 1

HCID 178441558HCID 178441558, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

3-[2-tert-Butyl-4-(4-fluoro-2-aminophenyl)-1H-imidazol-5-yl]-2-fluoropyridine (0.070 g, 0.21 mmol) was dissolved in ethanol (2 mL). The reaction was heated in a microwave reactor at 180° C. for 5 min. The reaction was concentrated and purified by column chromatography on silica gel (50% ethyl acetate 50% hexanes) to give 0.052 g of the desired product. 1H NMR (500 MHz, CD3OD): δ 8.16-8.18 (m, 1H), 7.85-7.87 (m, 1H), 7.48-7.51 (m, 1H), 7.07-7.10 (m, 1H), 6.82-6.90 (m, 2H), 1.58 (s, 9H). MS [M+H]=309.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography on silica gel (50% ethyl acetate 50% hexanes)

Sources & evidence

ORD record
ord-8017c82308a543e8b2cdb46267b5d818
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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