Trifluoroacetic acid → HCID 66970398, compound

HRID 1361651Notes

Reaction equation

HRID 1361651 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[F:24])[C:18]([OH:20])=[O:19].N(CC)(CC)CC.FC(C(O)=O)(F)F.C(O)(C(F)(F)F)=O>C(O)(C)C.CCN(CC)CC>[F:24][C:23]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=1[NH:14][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 753963-Amino-4-fluorobenzoic acidHCID 12210277Triethylamine; trifluoroacetic acid2×HCID 161089744-(2-Chloropyridin-3-yl)pyrimidine

Product 1

HCID 66970398HCID 66970398, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

4-(2-Chloro-pyridin-3-yl)-pyrimidine (240 mg, 1.2 mmol), 3-amino-4-fluorobenzoic acid (217 mg, 1.40 mmol), and 340 mg Et3N-TFA salt were mixed together in a sealed tube under argon. (The liquid Et3N-TFA reagent was generated by adding 2.5 mL TFA dropwise to a 0° C. solution of 3 mL Et3N in isopropanol, then concentrating by rotary evaporator followed by 30 minutes under high vacuum.). The mixture was melted at 95° C., and heating was continued overnight. The residue was triturated with a small amount of methanol and filtered to obtain the title compound as a solid. MS m/z=311 [M+H]+. Calc'd for C16H11FN4O2: 310.29.

Workup

  1. concentrationconcentrating by rotary evaporator
  2. temperatureheating
  3. waitwas continued overnight
  4. customThe residue was triturated with a small amount of methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-dab026e1a574415eb425ed8f344139c1
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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