Ammonia → 1-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-benzyl]-3-(3-trifluoromethyl-phenyl)-urea

HRID 1446736Notes

Reaction equation

HRID 1446736 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.C(N(C(C)C)CC)(C)C.[F:28][C:29]([F:40])([F:39])[C:30]1[CH:31]=[C:32]([N:36]=[C:37]=[O:38])[CH:33]=[CH:34][CH:35]=1.N>CO.C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:18]=[CH:17][C:14]([CH2:15][NH:16][C:37]([NH:36][C:32]4[CH:33]=[CH:34][CH:35]=[C:30]([C:29]([F:28])([F:39])[F:40])[CH:31]=4)=[O:38])=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 81531DiisopropylethylamineHCID 68546763HCID 68546763, compound

Product 1

HCID 685391571-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-benzyl]-3-(3-trifluoromethyl-phenyl)-ureaYield 50.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Charge a 50 mL flask equipped with a magnetic stir bar, 4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-benzylamine (720 mg, 2.79 mmol), di-isopropyl ethyl amine (723 mg, 0.93 mL, 5.6 mmol), and THF (28 mL). Purge the flask with N2, and add 3-trifluoromethylphenyl-isocyanate (1.04 g, 0.77 mL, 5.6 mmol) via syringe. Mix the reaction at room temperature for 24 hours. Evaporate the reaction in vacuo, and chromatograph the residue using SiO2 eluting with a gradient of 1% to 15% of 2 M NH3 in MeOH with the balance CH2Cl2. Evaporate the fractions containing the product under reduced pressure, and vacuum oven dry the resulting ivory solid at 40° C. to give the title compound 624 mg (50.3%). MS(ES), m/z 445.3 (M+1).

Workup

  1. additionCharge a 50 mL flask
  2. customequipped with a magnetic stir bar
  3. customPurge the flask with N2
  4. additionMix
  5. customthe reaction at room temperature for 24 hours
  6. customEvaporate
  7. customthe reaction in vacuo, and chromatograph the residue
  8. customEvaporate the fractions
  9. additioncontaining the product under reduced pressure, and vacuum oven
  10. customdry the resulting ivory solid at 40° C.

Sources & evidence

ORD record
ord-f9f2d54002d44890804feca0b43d7c85
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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