Triethylamine → 1-(4-Chloro-3-(2-dimethylamino-ethoxy)-phenyl)-3-(2-methyl-quinolin-4-yl)-urea

HRID 2252088노트

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HRID 2252088 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.C(N(CC)CC)C.Cl[C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][C:34]=1[O:40][CH2:41][CH2:42][N:43]([CH3:45])[CH3:44]>C1COCC1>[Cl:32][C:33]1[CH:39]=[CH:38][C:36]([NH:37][C:21]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:12])[CH:3]=2)=[O:23])=[CH:35][C:34]=1[O:40][CH2:41][CH2:42][N:43]([CH3:45])[CH3:44]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 811164-Amino-2-methylquinolineHCID 94429TriphosgeneHCID 121354204-Chloro-3-(2-dimethylamino-ethoxy)aniline

생성물 1

HCID 589580961-(4-Chloro-3-(2-dimethylamino-ethoxy)-phenyl)-3-(2-methyl-quinolin-4-yl)-urea수율 114.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution containing 4-aminoquinaldine (74 mg, 0.46 mmol) in anhydrous THF (5.0 Ml) was added triethylamine (0.2 Ml, 1.4 mmol). The solution was cooled to 0° C. followed by the addition of triphosgene (45.0 mg, 0.18 mmol). The reaction mixture was stirred at 0° C. for 10 minutes before the addition of a solution of 4-chloro-3-(2-dimethylamino-ethoxy)aniline (100.0 mg, 0.46 mmol, for its synthsis see Steps 1-3 for Example 1) in THF (2 MI). The ice bath was removed and the mixture was heated at 65° C. for 2 hours before it was poured into a mixture of CH2Cl2/MeOH (20 Ml, 7:1 ratio). The resulting mixture was washed with 10% sodium bicarbonate (aq. 15.0 Ml). The organic layer was dried over MgSO4 and concentrated. The oily residue was chromatographed over silica gel (eluent: 20% MeOH in EtOAc) to give the desired product as an off-white solid (82.0 mg, 45% yield). The compounds of Example 15 and 16 were synthesized in the same manner as for Example 2.

후처리

  1. customThe ice bath was removed
  2. temperaturethe mixture was heated at 65° C. for 2 hours before it
  3. additionwas poured into a mixture of CH2Cl2/MeOH (20 Ml, 7:1 ratio)
  4. washThe resulting mixture was washed with 10% sodium bicarbonate (aq. 15.0 Ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe oily residue was chromatographed over silica gel (eluent: 20% MeOH in EtOAc)

출처 및 근거

ORD 기록
ord-390f5576a852483ea5c04890044bc37f
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320989B2

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