2-Fluoropyridine → HCID 178526823, compound

HRID 1819447Notes

Reaction equation

HRID 1819447 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.F[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1>>[N+:16]([C:15]1[C:10]([NH:9][CH2:8][C@H:5]2[CH2:4][CH2:3][C@H:2]([NH:1][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[CH2:7][CH2:6]2)=[N:11][C:12]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][C:28]([F:30])([F:31])[F:29])=[N:13][CH:14]=1)([O-:18])=[O:17]

Participants

3

Reactant 2

HCID 97462-FluoropyridineHCID 178511544HCID 178511544, compound

Product 1

HCID 178526823HCID 178526823, compound

Conditions

Temperature
165 °C

Procedure

A mixture of N4-[(trans-4-aminocyclohexyl)methyl]-5-nitro-N2-[2-(trifluoromethoxy)benzyl]pyrimidine-2,4-diamine (100 mg, 0.23 mmol), 2-fluoropyridine (0.5 mL) and diisopropylethyl (0.2 mL) was placed in a microwave tube and heated to 150° C. in the Personal Chemistry Microwave for 1 h, 165° C. for 1 h, then 185° C. for another 2 h. The reaction mixture was concentrated and the resulting residue was diluted with ethyl acetate. The organic phase was washed with 10% citric acid and brine. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 29 mg of the title compound, m/z 518.9 [M+1]+.

Workup

  1. customwas placed in a microwave tube
  2. concentrationThe reaction mixture was concentrated
  3. additionthe resulting residue was diluted with ethyl acetate
  4. washThe organic phase was washed with 10% citric acid and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-e863e01c88c84943beed92bddfa3e7d4
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…