Trifluoroacetic acid → HCID 11526341, compound

HRID 2117642Notes

Reaction equation

HRID 2117642 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][C:10](=[O:26])[N:11]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12]1[CH:17]=[CH:16][N:15]=[C:14](Cl)[N:13]=1.[CH3:27][N:28]([CH3:39])[CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1.FC(F)(F)C(O)=O>C(O)(C)C>[CH3:27][N:28]([CH3:39])[CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:14]2[N:13]=[C:12]([N:11]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:10](=[O:26])[O:9][C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=3[CH3:8])[CH:17]=[CH:16][N:15]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 64846554-[2-(Dimethylamino)ethoxy]anilineHCID 116248272,6-Dimethylphenyl N-(2-chloro-4-pyrimidinyl)-N-(phenylmethyl)carbamate

Product 1

HCID 11526341HCID 11526341, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A resealable tube was charged with the benzyl-(2-chloropyrimidin-4-yl)carbamic acid 2,6-dimethylphenyl ester (0.093 g, 0.253 mmol), 4-(2-dimethylaminoethoxy)-phenylamine (0.050 g, 0.278 mmol), and isopropanol (4 mL). Trifluoroacetic acid (0.072 g, 0.049 mL, 0.633 mmol) was added and the system was flushed with argon. The tube was sealed and the mixture was heated at 100° C. for 20 h. The reaction mixture was cooled to room temperature and concentrated to afford a pale purple oil. The oil was purified via column chromatography (gradient elution with 0-100% dichloromethane-(90: 10:1, dichloromethane/methanol/ammonium hydroxide)) to afford 2,6-dimethylphenyl 2-((4-((2-(dimethylamino)ethyl)oxy)phenyl)amino)-4-pyrimidinyl(phenylmethyl)carbamate as a white solid. MS (MH+) 512.3; Calculated 511.62 for C30H33N5O3.

Workup

  1. customthe system was flushed with argon
  2. customThe tube was sealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationconcentrated
  5. customto afford a pale purple oil
  6. customThe oil was purified via column chromatography (gradient elution with 0-100% dichloromethane-(90: 10:1, dichloromethane/methanol/ammonium hydroxide))

Sources & evidence

ORD record
ord-d5583715b2b8406aab1b470293a35f7c
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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