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

HRID 1446736노트

반응식

HRID 1446736 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-f9f2d54002d44890804feca0b43d7c85
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666879B2

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