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Trifluoroacetic acid → 4-Methyl-3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)benzoic acid

HRID 446276
Notes
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Reaction equation

HRID 446276 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[CH3:24])[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>[CH3:24][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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 755683-Amino-4-methylbenzoic acidHCID 12210277Triethylamine; trifluoroacetic acid2×HCID 161089744-(2-Chloropyridin-3-yl)pyrimidine

Product 1

HCID 161089754-Methyl-3-(3-(pyrimidin-4-yl)pyridin-2-ylamino)benzoic acid

Reagents, catalysts & solvents 2

HCID 3776
Isopropanol
Solvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
95 °C

Procedure

4-(2-Chloro-pyridin-3-yl)-pyrimidine (10.4 g, 54 mmol), 3-amino-4-methylbenzoic acid (19.4 g, 128 mmol), 17 g Et3N-TFA salt (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.), and 15 mL DMSO were mixed together in a sealed tube under argon. The mixture was stirred at 95° C. for 65 h. After cooling to RT, the residue was sonicated in 100 mL methanol to break up the solids, then filtered to obtain product as a yellow solid. MS m/z=307 [M+H]+. Calc'd for C17H14N4O2: 306.33.

Workup

  1. concentrationconcentrating by rotary evaporator
  2. addition), and 15 mL DMSO were mixed together in a sealed tube under argon
  3. temperatureAfter cooling to RT
  4. customthe residue was sonicated in 100 mL methanol
  5. filtrationfiltered
  6. customto obtain product as a yellow solid

Sources & evidence

ORD record
ord-70e6697b75bc42d48db99d661e03571b
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08476434B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes