Aniline → HCID 59381897, compound

HRID 2355079Notes

Reaction equation

HRID 2355079 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[C:13]([NH:18][C:19](=[O:31])[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[C:21]=3[CH3:30])[CH:14]=[CH:15][C:16]=2[CH3:17])=[O:10])=[CH:4][N:3]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH2:38])[CH:33]=1.FC(F)(F)C(O)=O.NC1C=CC=CC=1>CC(O)C>[CH3:30][C:21]1[C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]([NH:18][C:13]1[CH:14]=[CH:15][C:16]([CH3:17])=[C:11]([C:9]([NH:8][C:5]2[CH:4]=[N:3][C:2]([NH:38][C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)=[N:7][CH:6]=2)=[O:10])[CH:12]=1)=[O:31]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6422Trifluoroacetic acid2×HCID 100093-AminopyridineHCID 59381868HCID 59381868, compound

Product 1

HCID 59381897HCID 59381897, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

A small microwave reaction vessel was charged with N-(3-(((2-chloro-5-pyrimidinyl)amino)carbonyl)-4-methylphenyl)-2-methyl-3-(trifluoromethyl)benzamide 19 (0.100 g, 0.22 mmol), and pyridin-3-amine (0.10 g, 1.1 mmol) in IPA (1.0 mL). Trifluoroacetic acid (0.034 ml, 0.45 mmol) was added and the vessel was sealed. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 140° C. for 10 min. Monitored the reaction by LCMS and found 50% conversion. Added another 105 mg aniline and 0.05 mL TFA and resumed microwave heating the reaction at 140° C. for 15 min. After about >90% conversion was found by LCMS, the crude reaction mixture was filtered through a Buchner apparatus with micromembrane filter, and the filtrate was washed with copius amounts of MeOH to afford 2-methyl-N-(4-methyl-3-(((2-(3-pyridinylamino)-5-pyrimidinyl)amino)carbonyl)phenyl)-3-(trifluoromethyl)benzamide 20 as an off-white solid after drying. MS m/z found 507.1 [MH+], calc. for C26H21F3N6O2=506.17.

Workup

  1. customA small microwave reaction vessel
  2. customthe vessel was sealed
  3. customMonitored the reaction by LCMS
  4. temperatureheating
  5. customthe reaction at 140° C. for 15 min
  6. customthe crude reaction mixture
  7. filtrationwas filtered through a Buchner apparatus with micromembrane
  8. filtrationfilter
  9. washthe filtrate was washed with copius amounts of MeOH

Sources & evidence

ORD record
ord-34b0f69114004a768159ef6139765f4c
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Reaction notes

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